-Christen|37 years old|Living in WV in the US|I’m a dog(1 dog)& cat(I have 2 cats) mom -Pronouns are she/her -Supernatural lover since day 1 -Forever a Dean Winchester & Jensen Ackles woman -Have loved & adored Jensen since he was Eric Brady on Days of Our Lives -I’m a non shipper meaning I’m not into the whole shipping thing -Reblogs Fanfics I have read & reread over & over or is currently reading mainly Dean/Jensen fics. -Since I reblog fics that has explicit content in it this is an 18+ blog only! If you are under 18 please come back when older
Ok so I want to make a new pinned post to kind of give people a idea of what to expect on my blog. First off in case you didn’t read the mini bio under my avatar my name is Christen. I’m 35 and I’m from WV(West Virginia) which is in the US. I just want to let you guys know things I will discuss and things I won’t discuss. Since I am also fanfiction reader I will include a part in this post on what I will read and what I won’t read.
Just a quick note since I reblog explicit posts my blog is a 18+ only blog. If you are under the age of 18 please come back when you are older.
So I don’t take up everyone’s dash I will put everything under the “Keep Reading” thing. So read under the cut for about me, things I will & won’t discuss and fanfic stuff.
About Me:
Above I have already stated my age, name & where I am from. So I don’t see the reason in repeating it. I am a lover of Supernatural, The Boys, horror movies, true crime, many tv shows & movies, Disney and so much more. I am a lover of the paranormal I love any & everything creepy & spooky. I do think there are things in this world we can’t explain. I believe we are never truly alone and there is more than just this life we are living. Of course as everyone knows I am a HUGE lover of Jensen Ackles. I have been ever since I was 9 and saw him as Eric Brady on Days of Our Lives. My crush on him will never ever fade! I could go on more about myself but this post will be longer than I want it to be. I like to say I’m mix with sugar, spice & everything nice(bonus points if you get where I got that reference). All I ask for anyone on my blog is to be please be respectful. If you do that then we are cool!!
Things I will discuss:
I will pretty much discuss any thing just about. From my love of Jensen Ackles to anything that pops in my head. I can be very random at times. Whatever pops in my head I will most likely say it. So I hope everyone enjoys things I post. Of course most will be Jensen Ackles related. I can’t help it though. Oh just a warning I may take a bit to reply but I always do answer.
Just note things on my blog are of my opinion. If you do not agree with me that is fine. Just please be respectful about it. It’s okay to disagree on some things. Long as you are mature about it we have no problem.
Things I will not discuss & things I will not tolerate:
-I will not discuss politics at all. Politics can be a touchy subject. It never ends well when it is discussed. So I rather just avoid it at all costs.
-I will not tolerate any bullying or death threats to/towards anyone on my blog, to me, to celebrities or anyone period. I don’t like when people do that and will not tolerate it on my blog.
-I will not tolerate any hate towards Jensen or Jared on my blog. Both guys are amazing and they have great hearts. They don’t deserve the hate or harassment people send them.
-If I don’t want to discuss something I will let someone know it is not in my interest. So if I say that please don’t keep asking me over & over to discuss it if I say no I mean no.
-I am a non shipper which means I don’t go crazy over ships. It’s no secret I do not like Destiel or Cockles ship. I do not agree with the ship. Plus I have been bullied by many people in that ship cause I don’t like it. So I will not discuss anything Destiel or Cockles related.
FanFiction: *if you don’t read or write fanfics you can skip this part*
Long time ago I use to write fanfics but now I just read them. I only read Dean Winchester and Jensen Ackles fics. I do adore Jared/Sam but for some reason I just can’t read fics where he is the focus & not Dean/Jensen. I mean I see Jared/Sam as the best friend/brother type. So I am fine with Jared/Sam being included in fics as Dean/Jensen brother/friend. I am always up for suggestions for fics as well. So if you see a Dean/Jensen series I should read send them to me. Below will be fics I will & won’t read. So that way you know what to suggest.
Fics I read are: I mainly read Dean Winchester x Reader & Jensen Ackles x Reader. I also mainly read series cause I always want more of the story. But I do read one shots as well just that series are my favorite. Also nothing against ones that are Dean/Jensen x ofc(original female characters) I just like stories I can insert myself too. If I had a long day I just want to be able to lose myself in a story. If it’s x original characters I can’t do that. I don’t mind original characters being added to the stories. Just as long as the main point of the story remains Dean/Jensen x Reader(female reader of course). I do reblog fics I love so that way if anyone wants to they can read them.
Fics I won’t read or even touch include:
-Destiel/Cockles as I said before don’t agree with it or ship it.
-Wincest or any kind of incest period that is just nasty and gross.
-Underage fics I will not touch at all! I don’t mind some age gap fics but if one is underage and not legal I will not read it at all. Meaning if it has where reader is under the age of 21 and the other is in their 40s. I will not read it. That is still too large of an age for my liking any fics where the reader is under 21 is a no for me.
-Gross bathroom stuff that is disgusting and nasty
If any fics recommended to me is something I wouldn’t want to read I will delete the recommendation. If I think of anymore I will add it to the list. But that pretty much sums up my fanfic stuff.
That sums up just about everything for my blog. When I can I will probably update this pinned post to make everything look neater. But for now it will stay like this until I do that.
Also my asks are always open so if you like you can send me asks any time you want. You can ask me anything you want. All in all I hope you enjoy my blog!
I can’t believe what I am about to post is what brings me off lurking on here. But what happened at Purgatory Con in Germany I can’t stay quiet. Everyone who knows me knows I have been a fan of Jensen for a very long time. Basically ever since I was 9 and saw him as Eric Brady on Days of Our Lives I been hooked. So sometimes I feel protective over him. What happened at Purgatory Con pissed me off bad.
Of course in true fashion during a Jensen & Misha panel Misha had to start being disgusting about Dean & Cas. But then we get to the question of course a fan asked Jensen about Destiel. Every sane member of this fandom knows Jensen’s thoughts on the never will be non canon ship. He has said numerous of times over the years he did not play Dean that way. That Dean saw Cas as a brother a best friend he did not reciprocate romantic feeling. The person(can’t call them a fan at this point) started arguing with Jensen cause he didn’t give what they wanted. That person was basically telling Jensen he was wrong about his own character and his opinion. I have seen multiple people who was in that room stated you can tell Jensen was upset and was close to walking off stage. You know what he should have done it. Destiel shippers/hellers are why people think Supernatural fandom is toxic. It’s cause they are toxic over a stupid ship that will never be canon. They scream oh but the bi lighting etc lighting doesn’t describe someone’s personality. It’s just fucking lights nothing more. Some are thinking Jensen is being held hostage by networks to not say anything. No he isn’t cause if he was Misha wouldn’t be saying anything. It’s truly how Jensen feels about a character he played for 15 years. No it is not about inclusion cause CW was basically the number 1 station for queer stories. Jensen had a long week he had The Boys final episode plus whatever he is working on in LA. The man is constantly working. Plus he rarely does Supernatural cons outside of JIB & Creation. But he choose to attend the con cause he loves his fans. How do these fans repay him? By harassing him over a ship that will NEVER EVER HAPPEN AND WAS NEVER CANON! Hellers are not true fans of the show cause if they were they would know it wasn’t about romance. They are also not true fans of Jensen either cause if they were they would accept it and not harass him.
It’s to the point now where fans are calling Jensen names over it. Saying he is homophobic when he isn’t. I seen one fan say they stepped on his foot and was proud of it cause it was revenge he didn’t say it was canon. Worst part Misha basically started the damn shit. He keeps adding fuel to the fire by baiting them. He needs to grow balls and tell them to accept Jensen’s answer over his own character. To stop harassing him over this. But no Misha is a coward cause he needs them. Funny thing is they are the reason no one wants to hire him as an actor. Kripke only threw Misha a bone cause Misha begged to be on The Boys. But no one else will hire him cause they don’t want to deal with the toxic ass idiots who ships a ship that will never be canon and harass the actor over it. His actions and hellers are why I turned away from Misha & Cas.
For those thinking oh Jensen will change his mind he will see it since he is rewatching it with his kids. No he won’t Jensen has been firm on his opinion about for YEARS he is not changing his mind. I also want to add the staff at Purgatory con should be ashamed of themselves. They let fans harass Jensen over it. When they seen things were getting tense they should have ended it right there. But apparently whoever is in charge of Purgatory con are hellers too. It’s why they call it Heller con. But seriously they should be ashamed. I hope Jensen never does another purgatory con ever again. Cause if the staff can’t protect him like they should then he doesn’t need to attend. I hope he sticks to Creation & JIB because they will protect him unlike the staff of Purgatory.
Sorry this is long but shit like that pisses me off. Jensen didn’t deserve the treatment he got because fans can’t accept the ship will never be canon and Jensen will always say he played Dean straight.
Screen recorded Jensen’s interview from The Boys IG page during the season 5 premiere in Rome. Idk who the host is but dude is very awkward. But love that Jensen is wearing a dark green!! He is looking good!!!
Ps- sorry about the chat can’t hide those on IG live
I need help in locating a fic! It was a Jensen Ackles x Reader fic where jensen got in some trouble or something like that. He ends up having to be in Phantom of the Opera on broadway and he ends up meeting the reader. I can’t remember the fic name but I want to find it so bad help would be appreciated!
Before I post some other things there is something I want to address. During the weekend Supernatural con was in Austin Texas. We all know both Jared & Jensen love being in Austin. Jensen was happy to have spent time with Jared’s family. Jensen was even happy having fun at Saturday Night Special. Then he ended up having a bad Sunday why is that? Well cause of some rude ass fan or fans. I have heard now from multiple people who were at the con many who was right there when it happened. That some fan in line for ops said Jensen looks ugly now that the beard is gone. Jensen overheard this cause the fan was apparently loud and many said he was visibly upset the rest of the time. I noticed in photos and even during main panel something was bothering him. But I didn’t know that was why. If this is indeed true that fan better make all social media profiles private. I wouldn’t even call them a freaking fan to say something like that to or near him.
I have been a fan of Jensen since I was 9 years old and saw him as Eric Brady. I will be 37 in October so I have seen him without the beard. We all have especially in Supernatural as the closest he ever had to a beard was some stubble for Dean. So when Soldier Boy came and he had a full bushy beard it was interesting to see him like that. Then we get use to it use to him keeping it trimmed and then it’s gone again. Yeah I was like I will miss the beard. But I wound NEVER say he is ugly EVER. Jensen was filming from 7pm to 4am Friday the weekend he would have spent with his kids he spent with fans only to hear that bs! Jensen used to not like doing cons much cause Jensen is a shy person. He has come out of his shell more & more especially with singing. Then he hears a rude person cause at this point they are not a fan say something like that. I can imagine how he was feeling and it makes me want to hug him. Yes I will say Jensen looks good cause to me he always will. But the main reason I adore Jensen is cause of his heart. He has a big heart and did not deserve that. I did hear a few handlers said it too. Not sure if that is true if it is Creation needs new handlers.
Worst part I have heard fans say the same thing to Jared. If you spend all that money just to call any of those two ugly then you don’t need to be going to cons. Cause to say something rude like that you are not a fan. Remember they don’t have to do these cons but they choose to cause they love interacting with fans. Both Jared & Jensen are sweet beautiful people. They don’t deserve the rudeness some people give them. Next time if you wanna be rude about either of those 2 then keep yourself home. Cause those two deserve the world and deserve nothing but love and happiness. I never want to hear of anyone being rude to them like that ever again!
Sorry this is long but it irks me when people are like that to them. This is me next time I hear anyone being rude to either one again….
Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x Reader
Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, 100% a romcom (Wayne's Version 😜), angst, hurt, mentions of cheating, drinking, friendship
Word Count: 3.2k
Posted on Patreon May 8, 2025
A/N: It's truly rare to see so many of you call Dean an asshole. Reminds me of the good ol' Plastic Hearts days 😂 A lot of drinking, some well-needed friendship, and a few answers coming up in this chapter!
Main Masterlist|| Series Masterlist|| Tag List
Chapter 5: Old Habits
You don’t even realize how long you’ve been sitting behind the wheel of your mom’s car like you were seventeen again, crying over the same damn boy, until the knock comes. Soft but deliberate, like he knew you’d need a moment.
You jump slightly, wiping at your tear-streaked face before glancing to your left.
Cas stands outside the window, hands in the pockets of his weathered coat, blue eyes full of quiet sympathy. He doesn’t say anything right away – he just waits.
You roll the window down, swallowing the knot still thick in your throat.
“Hey,” he says gently.
“Hey.” Your voice cracks a little.
There’s a pause, the kind that only ever exists between people who’ve seen each other at their lowest. Then Cas nods toward the road.
“Come to Rocky’s with me?” he asks. “You look like you could use a drink.”
You consider it. Part of you wants to disappear into the night, curl up somewhere private and scream into the void. But another part, maybe the smaller, quieter part, just doesn’t want to be alone right now.
You nod slowly. “Yeah, okay.”
It’s the same old neon haze you remember. Pool table in the back. Booths with worn leather. It’s also a little too bright inside Rocky’s for the mood you’re in, but it’s comforting in its own way. Loud laughter, the clink of beer bottles, the low hum of classic rock through the speakers.
Cas pulls out a barstool for you by the counter and gestures you to sit.
You do. Well, you slump. Because who goddamn has the fucking energy?
Pamela places a tumbler with your favorite brand of whiskey and three shots of tequila in front of you like she knows you. She tilts her head and gives you a pitying look, and the only question she asks is:
“Dean?”
You exhale deeply through your nose and grab your first shot. “Yeah…”
Pamela nods with sympathy. “Figured something like this when the two of you came in here last night, behaving like you were teenagers again. Did you two steal that fucking fish?”
“Nope.” You shake your head half-heartedly and down your first shot.
Cas’ brow furrows, but you don’t notice it. You’re too deep into your whiskey and shot number two.
“Wait…” The creases on his brow only deepen when he glances at you like you’re a math equation he can’t solve. “You and Dean were here last night? Did you two spend the night together?”
You twitch your shoulders a little. “In a way, yeah… We didn’t sleep together if that’s what you were asking. We actually spent the whole day together. He found me here at Rocky’s before noon. We talked all night till the sun came up.”
“I-… Dammit, Dean.” Cas sighs loudly and suddenly seems irritated.
“What?” you prompt, your brow raising in confusion.
“We were having lunch together yesterday when Charlie’s group text came in, saying she just saw you at Rocky’s,” Cas tells you, and your heart stutters a little. “And Dean-… He-, uh, he suddenly gave me an excuse about some emergency, jumped up, and ran off.”
“What?!” Your jaw drops a little.
A lot, actually. Because why would he–
“I-… I didn’t think much of it at the time. He’s been a little off lately. Figured it was stress. Just thought it may have been some work emergency or last-minute wedding stuff,” Cas explains and lowers his gaze a little when your ex’s betrothal comes up.
“Right…”
“But now, I guess that makes sense,” Cas says and lets his eyes drift thoughtfully to the liquor shelf behind Pamela’s shoulder.
“So, he specifically came to see me?” you check, your eyes narrowing in.
“Uh…”
“You know, he told me he was just about to grab lunch,” you add, remembering.
Why would he–
Cas shakes his head and huffs. “No, he was already halfway through a burger when he just took off.”
“He left over half a burger to come see me?” Your eyes widen.
In Dean Winchester language, that’s practically a love declaration.
“See? Maybe there’s still something there. I’m not crazy,” you state, your heart swelling in your chest – probably from the booze, but who fucking cares?
“No, you’re definitely crazy. He’s getting married in six days,” Cas reminds you, trying to tame you like he’s done so many times throughout high school and college. It’s like muscle memory for him to keep a drunk group of friends in check.
“So who is she?” you ask like you want to scope out the fucking competition.
“She’s pretty cool, actually. Gets along well with everyone,” Cas replies casually.
“Sure,” you mutter and down your third shot. “I mean, if you love that whole hippie love child, ‘I don’t wear a bra or give a fuck what you think’ vibe, then she’s great.”
Cas scrutinizingly arches a brow at you.
You scoff and roll your eyes back. “Fine. Whatever. I’m not like that anymore. So, what? He’s marrying a younger, dream version of me? How old is she anyway?”
“She’s twenty-three,” Cas admits quietly in hopes it’ll keep your own voice down.
It doesn’t.
“Twenty-three?!” you gasp. “And he’s marrying her? Jesus fuck, what kinda blowjobs is she giving… How long have they been dating?”
“Uh, a little while…” Cas hesitates and clearly won’t supply you with the answers you need. He’s a good friend.
To Dean.
“Are you gonna tell me anything useful tonight?” you ask dryly.
“I’m gonna tell you when to stop drinking,” Cas retorts.
You sigh deeply and wish for more tequila. But you know Pamela won’t give you more. Not after you stole the fucking fish last night.
“I don’t get it,” you say after a moment. “Why would he do any of this? He took me on this whole crazy adventure last night. We went to all our old haunts. We kissed.”
“You kissed?!” Cas echoes a little louder.
“Who kissed?”
You recognize the voice behind you in an instant – Charlie. And as you glance over your shoulder, you see the others too – Benny, Sam, and Jess. It’s like time rewinds ten years, seeing all of them together again like you accidentally stumbled back into the friend group you used to be a part of.
But they all came for you.
“What the hell is this?” you ask, stunned.
Benny throws an arm around your shoulder. “What? You thought we’d leave you to drink your feelings away in solitude? You’re still one of us, chère.”
“I called in the cavalry,” Cas tells you with a wink. “Figured you could use some friends.”
Your smile turns a little bitter. “Right. ‘Cause we’re all still so goddamn close…”
They all glance at each other guiltily.
“Look, we-, uh, we just figured you were alright after you moved to New York,” Sam starts explaining. “And Dean, well–”
“Yeah, I know,” you huff quietly.
“What happened between you two back then?” Benny asks. “I mean, one minute the two of you were inseparable, and the next it was all over. Dean never said much about it afterward. We figured we just leave him be.”
You take a long breath and decide to finally tell your side of the story – the one that’s long been overdue. “I asked him to come with me to New York. He said no. Didn’t even think about it. Just… said no. I tried everything. I asked him to do long distance, that I’d come home every chance I’d get, that it wouldn’t be forever. Just till I got my first book published. But he didn’t wanna hear any of it. He gave me an ultimatum. Told me if I went, we were done, and I didn’t need bothering coming home again. That was it. No long-distance. No trying. Just… over.”
Benny whistles lowly. “Damn. That’s brutal.”
“You didn’t think to tell us that back then?” Charlie asks, clearly feeling guilty.
“I figured you’d all already picked your side,” you reply and give them a meek shrug of your shoulders. “I mean, I wasn’t part of this circle anymore. Not after I left.”
They all look at each other, visibly regretting the assumption.
“That’s on us,” Sam admits. “We should’ve called. Checked in. Something.”
“Well, here’s your chance to make it up to me,” you say, raising your glass with a tight grin. “Keep buying me drinks until I forget I ever came home.”
“So, can we get back to my earlier question?” Charlie prompts, and you recognize the familiar look of mischief in her eyes. “Who kissed who?”
“I kissed Dean,” you reply like it’s a question on a test.
“Wait, you guys kissed?” Sam’s brows quirk with brotherly bewilderment. “When?”
Ever the lawyer…
“Last night.”
“No shit!” Charlie’s mouth drops open.
“We’ve spent the whole day and night together like no time had passed. We drank at Rocky’s, we played shotgun mini golf, we talked all night like we were in love again…” you list, still trying to make sense of it yourself.
“Well, you know, maybe it was a closure thing,” Benny says and scratches his neck, as if he’s not even believing himself.
“Could be.” Cas gives a nod like he’s already sure (and in denial).
“He took me to The Lookout,” you add and say it like it’s common knowledge what that means in this town. “And you don’t take someone there unless–”
“You wanna hook up,” Benny finishes dryly.
“Didn’t you also lose your–” Charlie doesn’t have to finish the question, but you surely finish the whiskey in front you.
“Yep.”
The three boys all share a look, as if they were debating Dean’s mental health at this point.
“Well, let’s not jump to conclusions,” Cas says with an awkward little chuckle. “Maybe he did just take you there to talk. You guys do have a lot of history.”
“He kissed me back, okay?” you say bluntly. “I wanna make it very fucking clear that Dean Winchester rammed his tongue down my throat first.”
Jess snorts. “That would be a fun bumper sticker.”
“We, like, fully made out for several minutes,” you clarify. “I was this close to hopping into his lap and letting him recreate the night he took my virginity.”
Cas groans and pinches the bridge of his nose. “This is a disaster.”
“No,” Benny cuts in, raising a brow at Cas. “What’s a disaster is that you still think this was innocent.”
Cas frowns. “What do you mean?”
Benny crosses his arms, gives a shrug. “Well, they sure looked damn cozy to me at the diner. Shoulda seen how he looked at her, brother. He even put on their song at the jukebox and asked her to dance like it was junior prom all over again.”
“Alright, that’s it!” Exasperated, Charlie slams her palms on the counter. “There’s something you need to know–”
“Charlie,” Cas growls warningly.
“No, she deserves to know,” Charlie argues strongly. “We all know Dean’s been weird since the engagement.”
“She ain’t wrong.” Benny tilts his head and rubs the scruff on his jaw. “He’s been actin’ a little strange. Distant.”
“What, why?” You look between them in confusion.
“It’s not our place to tell,” Cas reminds them sternly. “Dean should be the one to tell her.”
Benny shrugs. “Dean ain’t gonna tell her, brother. Look, I love ‘im, but the guy’s like a turtle. Pulls in if you spook ‘im too much.” He thumbs at you. “And she’s a scary one.”
Benny and Charlie then share a look and give a united nod. Cas sighs in defeat and dramatically rolls his eyes back.
“So what’s the story?” you ask and notice the little flutter your heart does. You pull out your phone and open the notes app, your fingers eagerly typing away.
“What are you writing?” Charlie leans in a little over your shoulder to peer at your screen.
“Book,” you reply absentmindedly, then look up and smile. “Continue.”
“So, Dean and Jo met on Bumble,” Charlie starts almost conspiratorially.
“Wait, Bumble? The one where the girl reaches out first?” Your brows draw together so much you’re close to getting a migraine. “A guy like Dean Winchester should not be o–”
“–on there. Agreed,” Charlie finishes. “In cybersecurity, we call this a honeypot.”
“And get this,” Sam chimes in, like he’s decided he’s done with his brother’s bullshit, too. “They met like three months ago. I didn’t even know he was engaged till five weeks ago and Mom accidentally told me over the phone.”
“Three months?!” You’re speechless, and at the same time, you curse your brain for thinking that this chick apparently must be really, really, really good at giving head.
Benny picks up the story next. “They were only seein’ each other casually. Went on, like, four dates. Then she thought she was pregnant.”
“False alarm,” Charlie quickly swoops in to soothe your worries and answer your next question.
“Yeah, but Dean, God bless ‘im, apparently proposed before the timer went off,” Benny shares with an almost affectionate chuckle. “We think he might not know how to back outta it now.”
“Every time we bring it up, he shuts us down,” Sam mutters with that kind of annoyance in his hazel eyes that only a sibling could have toward another.
“Well, hey, that’s not entirely true,” Cas throws in, ever the defender. “Yes, he’s been acting a little… odd,” he admits slowly. “But he does like Jo.”
“Yeah, only ‘cause Jo reminds him of her,” Benny counters and snorts a chuckle, pointing at you.
Pamela, who’s quietly been listening, slides another glass of whiskey in front of you. You mouth an appreciative “thank you” and smile.
Cas groans before his phone buzzes. He glances down, frowns, then slides off the barstool next to you. “I’ve gotta call Meg. She probably wants ice cream… or attention. Be right back.”
He heads outside quickly, but none of you noticed the name on the screen wasn’t Meg. It was Dean.
And he’s waiting just outside.
Dean’s pacing outside Rocky’s like a man caught in a burning building with no exit in sight. He glances up as the door swings open and shuts, relief flashing briefly in his eyes before Cas’s expression snuffs it out.
“She’s in there,” Cas says flatly.
Dean exhales, slow and shaky. “Is she-, uh, is she okay?”
Cas raises a brow, arms crossing. “Define okay. If ‘okay’ means pounding shots like it’s a coping mechanism and publicly recounting the worst day of her life? Then yes, she’s fantastic, Dean.”
Dean’s brows pinch. “She told you about the kiss?”
“You mean after she told us you took her on a full-blown tour of nostalgia town?” Cas retorts wryly. “The diner, the song on the jukebox, The Lookout?”
Dean flinches, swallowing the giant lump in his throat that has formed hours ago and never seems to leave now.
“Yeah.” Cas gives him an even drier look. “Then she told us about the kiss.”
Dean opens his mouth, then shuts it again.
“She really thought it meant something, Dean,” Cas continues. “I mean, for a minute there, so did I.”
Dean’s voice is hoarse. “I wasn’t trying to–”
“What?” Cas cuts in, arching an eyebrow. “Lead her on? Reignite ten years of history with a smirk and a slow dance and think she’d just, what? Forget all of it in the morning?”
Dean runs a hand through his hair, jaw clenching. “I didn’t mean for it to go that far.”
Cas huffs a humorless laugh. “That’s what you said about Jo, too.”
Green eyes narrow sharply at his friend.
Dean mutters, “I’m trying to do the right thing.”
“By who?” Cas snaps. “Jo? Your family? Your high school ex? Yourself? ‘Cause I gotta tell you, Dean, no one in there thinks this wedding is a good idea anymore.”
Dean straightens up, stiff. “Jo’s a good person.”
“I’m not saying she isn’t,” Cas replies softly. “I’m saying she’s not your person. Jo’s like her, you know… You picked someone who reminds you of her. Just… less complicated. Less pain attached.”
Dean doesn’t argue. He averts his gaze to the pavement, molars grinding.
Cas sighs. “You know I didn’t say anything back then because I figured maybe – maybe – it could work. Maybe she’d be good for you. But now?” He gestures toward the bar. “Now I’ve seen what you’re like around her again. And I think you’re about to make the biggest mistake of your life.”
Dean swallows harshly, nodding. “You think I don’t know that?”
“Do you?” Cas shoots back. “Because you’re still standing here pretending this whole thing was just a blip. Like you didn’t spend an entire day and night with her and acted like she was the only person in the damn world.” He shakes his head and scoffs a bitter laugh. “You want to know what really broke her, Dean? It wasn’t the kiss. It wasn’t even the day you spent together. It was telling us about the break up. About how she offered you every option. Offered to try, to make it work long-distance, and you shut her down.”
Dean’s lips tighten into a thin line.
“You told her she had to choose. So she did. She chose herself. And you’ve been punishing her for it ever since.”
Dean exhales like it hurts.
“And even then,” Cas goes on and takes a step forward, blue eyes narrowed, “she protected you. For ten years. She let everyone believe she just left. She never told us what really happened. Neither did you.”
Dean’s voice is rough when he speaks, “She said she wasn’t gonna tell anyone.”
Cas’s tone turns cold. “Well, congrats. Guess you finally pissed her off enough to stop defending you,” he mutters. “You didn’t tell me any of this yesterday. You disappeared mid-sentence. Left me sitting in the middle of lunch after Charlie’s group text came in.”
“I was gonna–”
Cas raises a hand. “Spare me.”
“It was complicated. I just–… I had to see her, alright? I just had to.”
Cas gives him a long, tired look. “You’re in love with her. You never stopped. And now you’re marrying someone else because you think you have to.”
Dean stays quiet.
“You’re not the only one confused, you know,” Cas adds. “She came back here thinking you were just some guy she used to love. But then you looked at her like that, took her to all those places, kissed her, and now she doesn’t know which way is up anymore.”
Dean nods once, barely. “Just… make sure she gets home safe tonight.”
“Sure. I’ll do what you couldn’t,” Cas replies dryly. “Cut her off. Drive her home. Not take advantage of her.”
Dean’s shoulders flinch at his friend’s words, his mind racing with regret, heart flooding with guilt.
Cas steps back toward the door. “You still have a choice, Dean. But if you wait too long, you’re gonna lose the best thing that ever happened to you. Again.”
He doesn’t wait for a reply as he walks back inside, leaving Dean outside in the dark, drowning in everything he can’t bring himself to say.
▶️ Chapter 6: Old Battles – AUGUST 6
Are you applauding for Cas or reader's drinking skills this chapter? Also, Dean on fucking Bumble… Can you imagine the influx of messages a guy like that would get? 🤯🤣
Coming Up:
Dean stands close to the barbecue, nursing a sweating beer bottle and a headache that’s been building since breakfast. It’s sunny. It’s humid. It’s hell. And the absolute last person he’s expected to see crossing the lawn like a goddamn sunflower in bloom, is you.
“Fuck me,” he mutters under his breath, trying not to drop the bottle.
You’re still smiling. Like this is goddamn casual. Like you didn’t drop a nuke on his life two nights ago. Like you didn’t kiss him like you meant it – and then promised to fucking disappear forever.
Instead, you saunter up to his mother with a kiss on the cheek, arms wide, a little twinkle in your eye like you know exactly what you’re doing. Because of course you do.
Mary beams like she’s just won bingo and America’s Got Talent in the same day. Because of course she does. Dean knows what she’s been doing and also knows his mother can never resist meddling in his life.
His heart is already racing – and not in the fun way. He stares at you, at that stupidly gorgeous smile, and tries to play it cool, but it doesn’t work. Your head tilts just slightly, lips twitching like you’re holding back a laugh. You lift your fingers in a little wave.
Whew okay NOW I am caught up but I’m still mad at you Wayne! I don’t like yelling at Dean cause he is my sweet teddy bear! But he was bad!!
Her drinking the feelings away girl same! If only it was that easy though. The fact Pam asked about the fish had me snorting a bit. 😂 Cas, Sam, Benny & Jess coming was so sweet! She thought they wouldn’t be there for her you can tell they feel bad she thinks that. Then she tells them the story. I love how they are on her side cause poor girl is hurting. Dean using Bumble though omg! 😂
Soon as Cas’s phone buzzed I went that’s Dean! Sure enough it was I was like no Dean bad Dean you don’t deserve to go in there! Then Cas laying into him! Cas had me going…
Dean may not like it but Cas told him the truth. I’m glad he stood up for her. Cas gave him the reality check he needed! Now Dean better FIX IT! Before it’s too late cause I hate yelling at Dean!
Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x Reader
Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, 100% a romcom (Wayne's Version 😜), major angst alert here, cheating, hurt & heartbreak
Word Count: 5.6k
Posted on Patreon April 30, 2025
A/N: Ooof, Dean surely fucked up here, but before you pull out the pitchforks for me, I promise this is only the heartbreaking climax (you know the point in the romcom where you scream at your TV), but I will fix it in the following chapters with the usual dose of Wayne humor 😜❤️🩹
Main Masterlist|| Series Masterlist|| Tag List
Chapter 4: Old Scars
The words fill pages faster than you can hit the keys. Your mind is reeling. The inspiration is flowing.
Spending a crazy night out with an ex, reliving your past? Inspiring. Bye-bye, writer’s block!
Sure, Dean’s abrupt rejection at the end of the night was fucking brutal. It was the worst possible thing that could’ve happened as far as reunions with exes are concerned.
In an ideal world, you would’ve simply wowed him, and he would’ve been speechless and fallen to your feet, telling you what a grave mistake letting you go was and begging you to take him back.
Which, granted, sort of happened. He said and did all the right things – up until that very end. You still don’t know what happened. Is this the last memory the two of you have created? Is this the closure you’ve been waiting for?
Is it over now?
It doesn’t feel like it. You can’t get every word, every action of his from last night out of your head. It’s tugging at your heart.
There has to be an explanation. The two of you should at least talk about what happened. Why did he stop it?
You felt like both of you had been on the same wavelength. You had talked about your feelings and your break-up, and it was all good and healthy and surprisingly mature.
Is he scared you’d leave again? But you don’t have to. You thought you’d made that clear. Maybe you hadn’t.
You probably should.
With that in mind, you finally emerge from your childhood bedroom after three hours of sleep and five hours of writing. Determined to talk to Dean, you march downstairs and find your mother with her lover in the kitchen. Thankfully, decently clothed and not in any way entangled.
“Hi, honey! I was starting to worry you wouldn’t wake up at all, sleepyhead,” your mother greets you with a soft smile. “I made you your favorite breakfast.”
“Oh, thanks, Mom. But I’m not sure I can eat right now,” you tell her apologetically. Your still nauseous stomach agrees with you.
Shotgunning beer and God knows what else are a surefire recipe for a terrible hangover, although you feel better than you did a few hours ago.
“I figured we could hang out today. I haven’t really seen you since you got here,” your mother says. “Maybe we could take a walk or see a movie?”
The guilt bubbles in your stomach, but to be fair, you, on other hand, have already seen plenty of your mother in a short amount of time. Still, you’ve come here for her and want to spend time with her, even when it’s not always easy. But you need to speak with Dean first and free your mind before you can concentrate on your mom again.
“Uh, can we postpone that to tomorrow, maybe? I-, uh, I was wondering if I can borrow your car? I need to go see Dean today,” you tell her. One good thing about your mother is that she’s probably the most understanding person on this planet.
There literally is nothing you can’t tell her.
“Sure, honey.” She smiles, nodding. “I didn’t know you were seeing Dean again. How is he?”
“Uh, fine. I think…” you reply.
“Please give him my best,” she says happily. You know she’s always loved Dean. Who could blame her? He was the perfect high school boyfriend – protective, respectful, kind.
“I will.”
“Oh, and honey?” You turn in the doorway to look at your mother with a raised brow. “You look so pretty today. Your boobs look amazing in that dress. You fucking got this.” She winks.
“Thanks, Mom.” You smile with pink cheeks at her confidence boost.
Yeah, your mom can be pretty fucking great sometimes – if one of your former teachers isn’t balls-deep inside of her.
It feels like a lifetime ago, like everything else in this town, when you drive down the familiar street of Dean’s neighborhood. The sage green Winchester family home comes into view and right next to it, you also find the home Dean has built for himself.
It’s even more beautiful than the pictures have shown and unlike anything else in the area. It’s sleek and black, much like his beloved car, and entirely made out of wood, with big windows in the front that reach to the roof.
Your heart pounds relentlessly as you park by the curb and stroll up the small path between the dark green grass and trees. And even though you’re nervous he’ll turn you down again, you’ve promised yourself you wouldn’t run away this time – not until the two of you have talked it all out and laid all the cards on the table.
Your knuckles hesitantly tap on the front door. By the time it swings open, your heart is ready to leap out of your chest.
And well, your breath halts when Dean Winchester stands flawlessly in front of you again. It should be a damn crime to look this perfectly handsome.
“Oh, Y/N… Hey.” Dean’s brow shoots up once he recognizes you.
Your heart stops abruptly. He doesn’t seem happy to see you. There’s no smile on his plump lips, only panic in his green eyes. It’s not a good sign that necessarily boosts your confidence.
Neither is the fact that he quickly steps out onto the porch and shoves the door almost entirely shut behind him, only leaving an inch of leeway. While he doesn’t say it directly, he’s surely not planning on inviting you into his home.
He has also called you by your name instead of the endearing “sweetheart.”
Fuck. Maybe this is another bad idea of yours. He’s clearly not thrilled about your visit.
“Hi, uhm–,” you finally manage to spit out and offer a tentative smile, your fingers fidgeting with the sleeves of your old jeans jacket. “Look, I would’ve texted you that I was coming by, but I don’t have your number anymore, so…”
What a fucking great start…
“Right, yeah.” Dean nods, hand reaching back to scratch the nape of his neck, green eyes flicking back to the front door like he wants to flee this conversation.
“I just wanted to apologize for how things ended last night… or this morning or whatever,” you say.
“No, uh, no, don’t worry about it, okay?” Dean says swiftly and chuckles slightly, which makes your brow raise.
You know that laugh. It’s the fake one, his whole body language screaming that he’s uncomfortable with this situation right now.
“I just figured we should talk about it, you know? I don’t want there to be a misunderstanding,” you tell him and try to hold his gaze, but Dean’s eyes keep escaping yours. “Look, last night was perfect, and everything I said is true, okay? I regret leaving, I regret breaking up, and I can write anywhere I want. I mean, I wrote twenty pages today after spending only a day with you. I don’t need New York. All I need is you. I wanna come back. And I wanna be with you.” You watch Dean suck in a breath. “If you want that, too?”
Your brow weaves into insecure little knits as the seconds tick by and Dean doesn’t say anything. You’re not even sure he’s breathing at this point. Is his heart still beating? Should you call 911?
“Dean?”
Dean’s mouth parts like he’s about to say something – maybe to let you down gently, maybe to kiss you senseless – but whatever words he’s searching for never make it out.
Because that’s when the front door creaks open again behind him.
“Dean? Honey, who’s at the–… Oh!” a familiar voice cuts in, bright and nostalgic.
Dean turns too slowly to stop it, and there she is: Mary Winchester, just as beautiful and composed as you remember her. Her apron is dusted with flour and something red – probably the homemade marinara she always used to brag about. Her eyes land on you, and her expression shifts instantly from curiosity to delighted surprise.
“Y/N?” Her voice lifts in that sweet, sing-songy way you haven’t heard in a decade. “Oh my God, look at you!”
Your nerves twist into something warmer, something almost safe. “Hey, Mary.”
“Oh, come here,” she says, stepping right past Dean, who looks like he’s trying to disappear into the woodwork. She pulls you into a tight, motherly hug that smells like rosemary and red wine. “Ten years, and you still look exactly the same. My goodness. I can’t believe this!”
You laugh softly into her shoulder. “You look amazing.”
“Well, flattery will get you seated at the dinner table,” she teases, stepping back but keeping her hands on your arms like she’s afraid you’ll vanish again. “Are you back in town for good? Passing through? Tell me everything.”
Dean clears his throat sharply behind her. “Mom, actually, she was just about to lea–”
But Mary only glances over her shoulder with a quick, “One second, honey.” Then she turns right back to you. “You’re staying for dinner. We’ve got everyone over tonight. It’s a whole thing. Don’t even think about saying no.”
“Oh, I don’t want to intrude. I didn’t know you were having a whole family thing tonight.” You glance at Dean again and see him avert his eyes once more, swallowing. “I’ll come back another time.”
“Nonsense!” Mary cuts in, unbothered. “Please. You’re family. You’re not intruding. I won’t take no for an answer.”
You look at Dean, who seems like he’s about to spontaneously combust. His green eyes flash with something sharp – maybe warning, maybe dread.
“Mom, I don’t thin–”
Mary, however, is on a roll. “Come on in, sweetheart,” she says as she nudges the door fully open. “Dean, help her with her jacket, will you?”
Dean hesitates, then obeys with that tight-lipped smile he uses when he’s forcing himself to play nice. He lets out a deep, long sigh and then follows you two inside.
The warmth of the house wraps around you the second you step inside, muffling the nerves still dancing in your chest. It’s louder than you expected – voices and laughter carrying from the dining room, music humming low in the background, something sizzling in the kitchen.
You barely have time to take it in before you hear a voice behind you.
“No way,” someone says, familiar and warm.
You turn, and there’s Sam – taller than you remember (which seems impossible), broader too, with a clean-shaven face and a button-up rolled at the sleeves. He breaks into a wide grin, crossing the space in just a few long strides.
You don’t have time to respond before you’re pulled into a tight, brotherly hug. His height still makes you feel like you’re being swallowed up, and you laugh as you hug him back.
“Damn, it’s been forever.”
You laugh into his shoulder. “Yeah, about ten years.”
He pulls back to look at you. “Dean didn’t say a word you were coming.”
“Wouldn’t be Dean if he did,” you say, forcing a smile. You glance toward the kitchen. Dean has disappeared to somewhere in this house as soon as you set foot inside. “It was kind of a last-minute thing.”
“Well, it’s awesome you’re here.” Sam gestures toward the living room. “Jess is gonna freak.”
He leads you around the corner, and there she is – Jess, glowing in a loose summer dress that clings gently to a small but clear baby bump. Her eyes go wide when she sees you.
“Oh my God,” she says, already walking toward you. “Y/N!”
You exchange a quick hug, softer than the one with Sam, but familiar.
“It’s been forever,” she says, pulling back. “I think we met that one weekend when you and Dean were visiting Sam at Stanford.”
You nod as the memory floods your mind. “You’d just started dating Sam, and we were helping him move into that awful apartment.”
Jess snorts. “The one with the bathroom window that didn’t close? I remember. You and Dean carried, like, everything and build that IKEA shelf.”
“It was the worst shelf in California,” you say, grinning. “Congrats, by the way.”
“Thanks. October.” Jess places a hand on her belly instinctively. “And Sam opened his own practice,” she adds, clearly proud.
“Palo Alto,” Sam confirms with a modest shrug. “Started small. We’ll see how it goes.”
Before you can answer, Sam turns suddenly. “Hey, have you met Jo yet?”
You freeze as a young woman in her early twenties that you’ve never seen before at a Winchester family gathering steps in from the hallway, tucking a loose strand of blonde hair behind her ear. Her eyes find yours quickly, guarded but polite.
“Jo, this is Y/N,” Sam introduces you two.
Jo’s smile falters for only a second before she recovers. “Hey. Nice to meet you.”
“Yeah, you too,” you manage, not missing the way her gaze lingers just a little too long.
“Mary probably needs help in the kitchen,” Jo says quickly, already moving past you and disappearing through the swinging door, leaving you behind with a furrowed brow and sheer confusion.
Before the silence can stretch, however, a soft, deep voice cuts in.
“Y/N.”
You turn to see Castiel standing by the doorway, blue eyes calm and unreadable, his tie slightly askew like always. There’s something grounding about him, something familiar. Probably because he hasn’t changed that tie since high school. Yeah, he's always been a bit odd.
“Cas,” you say, exhaling. “Hey.”
He pulls you in for a hug, lingering for a moment like he’s checking that you’re real. When he steps back, he tilts his head.
“I didn’t know you’d be here,” he says, brow slightly knitted and exchanging a look with Sam.
“Yeah, I didn’t exactly send out a memo. Was a spontaneous thing.”
He nods slowly, studying your face. “This is… an odd situation.”
You huff out a quiet laugh. “Yeah, tell me about it. Showing up to a family dinner at your ex’s? Not exactly what I pictured when I came back to visit my mom for a few days.”
Cas blinks, brow creasing a little more. “No, I mean given the-, uh, the timing.”
You cock your head. “Timing?”
His eyes flicker like he’s trying to figure out how much you know. But before he can say anything else, you wave it off with a wry smile.
“I get it. It’s super weird. But I’m just here to talk to him. Clear the air, you know?” you assuage.
You don’t want to cause drama; you just have to sort through your own feelings and get on the same wavelength with Dean. But Cas wouldn’t be Cas if he isn’t worried.
Cas nods slowly, though his expression stays unreadable. “Right. That makes sense.”
You glance around the room. “Everyone seems happy.”
“They are,” he says. “Mostly.”
Before you can ask what that means, Mary’s voice floats in from the dining room.
“Dinner’s ready! Come grab a seat, everybody!”
The clatter of silverware and soft hum of conversation fill the room as everyone settles into their seats. The dining table is long and wooden, and it’s set beautifully with mismatched floral plates, linen napkins, and an abundance of food – roast chicken, roasted vegetables, steaming bowls of potatoes, and enough bread to feed an army.
You slide into your seat between Sam and Cas. Jess sits beside Sam, and there’s an empty spot next to Cas, presumably for Meg, who is too pregnant to still waddle around. Or as Cas tells you – too cranky.
Across from you, a few seats farther up, Jo sits next to Dean. She seems sweet. Helpful. Maybe a longtime family friend who’s just close with Mary. You don’t think much of it when she passes you the basket of bread with a smile or jokes with Jess about baby names.
Dean doesn’t even look at her. Doesn’t really look at you either. His jaw is locked tight and his green eyes are focused entirely on his plate. You don’t know what’s going on, even though your ever-knotting stomach is trying to warn you.
Why is he not looking at you? Why is he avoiding you? Why isn’t he sitting next to you and trying to figure out this spark between you two like you do?
You try your best to ignore those feelings and do your best to smile as Mary moves around the table, pouring wine into glasses and insisting everyone try her sweet potato gratin. Maybe it’s just all in your head. You know a family gathering isn’t ideal to talk about your relationship with Dean. The two of you should do this alone, not with an audience of nosy relatives and friends.
Cas gives you a small, grounding smile, and Sam leans over now and then to crack a quiet joke, helping ease the tension in your shoulders. And just for a second, it feels okay.
Then John stands up at the head of the table. The room hushes around him like it’s muscle memory for everyone.
John raises his glass. “Well, hell,” he starts with a dry chuckle. “Look at this table. All of us here again. That doesn’t happen much anymore.”
Scattered murmurs and laughs of agreement follow.
“It means a lot to have everyone home,” John goes on, glancing at Sam and Jess. “Sam, Jess – we’re so proud of you both. You’ve made a good life out west. And I know Meg would be here too if she could be.”
Cas nods softly beside you.
“And,” John adds, his eyes flicking to you, “it’s good to have some old faces back in town as well.”
Your chest tightens at that. You give a small smile, lifting your glass. You find Dean’s eyes, still smiling, but it fades when he averts his gaze again.
“But tonight’s really about two people who are about to start a new chapter,” John continues. “So if you’ll all raise a glass to the bride and groom–”
You freeze. The smile on your lips drops, as does your heart. You blink and glance toward Cas, brows furrowing.
“Wait… Who’s getting married?” you whisper, your voice just audible under the din of chairs shifting and glasses clinking.
Cas turns toward you slowly, confusion flickering over his face. “You-… you don’t know?” he asks, voice low and hesitant.
You shake your head, feeling the blood drain from your face.
That’s when Sam turns, catching the exchange. He looks at you, then at Cas, then quickly up the table – just in time for the next line.
“To Dean and Jo,” John says proudly.
The sound of clinking glasses is distant, muted by the rushing in your ears. Your eyes snap across the table.
Dean.
Dean is already looking at you. And this time, you catch it. The panic. The guilt. The helpless ache in his green eyes. He knows exactly what this moment means, what he’s done, what he let happen.
Then he breaks the stare, dropping his gaze in shame. Beside him, Jo leans in with a bright smile and innocently presses a kiss to his cheek.
Something in your chest splits, clean and sharp. Your throat tightens. You want to scream but can’t.
So, you do the only logical thing and pick up your wine glass, downing the whole fucking thing in one go. You know Dean is watching you again, guilt, shame, and worry still the most prominent features in his eyes. Cas and Sam are watching you, too.
Cas’ brows lift slowly in what might be concern or judgment. You’re not sure which. You set the empty glass back down with a frustrated thud.
Sam’s face, on the other hand, morphs from confusion to horror, then rage, then disbelief. He turns toward Dean with a look that says: What the actual hell, man?
They stare at each other for a beat. Two brothers having a silent war with their eyes across the dinner table. Sam’s jaw tightens. Dean blinks slowly like he wants to disappear into the napkin on his lap.
Cas then leans back in his chair and looks at Dean as well with a quiet, scolding glance that says everything he doesn’t.
And you? You don’t say a word because if you open your mouth now, you might not stop screaming, yelling, and crying. You don’t want to cause a scene, so you just wait for your glass to be refilled and this dinner nightmare to be finally fucking over.
You slip your arms into your jacket, shoulders still tense from dinner, and you’re not sure if you ever get rid of those knots again – especially the ones in your heart. The house is still full of lively sounds – clattering dishes, Jess’s soft laughter drifting in from the living room, Sam’s voice somewhere down the hall. Everyone’s settling into the post-dinner lull. Everyone except you.
Dean hasn’t come near you since the toast, and you don’t expect him to.
“I should probably head out,” you say, offering Mary a warm smile as she folds a dish towel by the sink.
She looks up, smile still lingering on her lips, but something flickers in her eyes. “Already? You sure?”
You nod. “Yeah, I promised my mom I’d spend some time with her while I’m here. I’m not in town long.”
And you sure as fuck don’t plan on staying in Lawrence any longer now.
Mary steps closer, drying her hands. “Well, before you go, I wanted to ask if you’d come to the wedding?”
You blink. “Oh.”
Yeah, you sure as hell aren’t planning on doing that either. Why don’t they all just shoot arrows at your heart? It would yield the same results at this point.
“It’s this weekend,” she continues quickly, like she doesn’t want to give you time to say no. “I don’t want to put you on the spot, but we would love to see you there. I’m sure Dean would, too. We could really use the extra hands, you know? Decorations, music, seating… You’ve always had an eye for that kind of thing.”
Somehow you have a hard time believing her that Dean actually wants you there. He clearly didn’t even want you at this dinner tonight – for obvious reasons – and at this point, you’ve surely seen enough of your lying, piece-of-shit ex-boyfriend.
Honestly, can anyone blame you for being mad at him? And “mad” isn’t even the correct word for what you’re feeling.
You’re fucking livid and heartbroken – just like you’d been ten years ago.
“Oh, that’s kind of you,” you say, treading carefully, “but I think it’s best if I–”
“If not the wedding,” she interrupts, not missing a beat, “we’re doing a small get-together tomorrow afternoon. Down by the river. Just family and a few close friends. Food, drinks, swimming if it’s warm enough. You’d be more than welcome, sweetheart.”
You hesitate. The polite thing would be to say no again. But her gaze is steady, hopeful, and full of something deeper – something unspoken.
“I’ll think about it,” you say gently and decide to lie.
Hell would have to freeze over first before you even set a pinky toe next to Dean again. At this point, you’re inclined to name him “The Lord Voldemort of Ex-Boyfriends” – never to be spoken of again unless it’s a whispered hush when you’re blackout drunk.
But Mary buys it and smiles, satisfied. “That’s all I ask.” She hands you a container of leftovers, and just before you open the front door, she squeezes your arm. “It was really good to see you again.”
“You too,” you say, voice a little softer now.
John doesn’t wait long after the door closes. He’s standing by the kitchen counter, watching his wife with arms crossed and an expression that’s a mix of exasperation and resignation.
“You really invited her to the wedding?”
Mary wipes the counter with slow, deliberate strokes. Innocent. “I invited her to the river tomorrow. She can make her own decision after that.”
John huffs, rubbing his scruffy jaw. “You know Dean won’t like this.”
“I’m not doing it for Dean,” Mary replies. “I’m doing it because of him. I’m doing what any mother would do. I’m protecting my son from making a mistake he’ll spend the rest of his life regretting.”
John shakes his head. “He asked you for the ring again last week. You think this helps?”
“He’s asking for something he’s not ready for,” she replies stubbornly, tossing the rag in the sink. “And deep down, I think he knows it.”
John leans against the counter, scratching the back of his neck in exhaustion. “You promised him that ring when he was a kid, Mary. You made a big deal out of it.”
“I promised it to my oldest son when I believed he’d give it to someone who was good for him,” she says, firm but quiet. “I still believe in that promise. He just hasn’t made the right choice yet. You see the way he looked at her tonight?”
John sighs heavily. “He’s confused. You’re stirring things up. You don’t think him asking for that ring is him fighting for what he wants? You’re gambling with his heart.”
“No, I’m reminding him who had it first,” she argues with the same Winchester stubbornness. “He’s settling, and I think he’s scared to admit that. We both know how this wedding came to be. Honestly, I don’t understand why you can’t talk to him. You know he’s probably only doing this for you.”
John falls quiet for a beat, jaw working. Then he lets out another deep sigh and resigns. “I hate this fighting between you two.”
“I hate it too,” Mary admits, her voice softer now. “But I’d rather have him hate me for holding onto the ring than live the rest of his life wondering what if.”
John looks down at the floor, then back at her with something softer in his eyes. “You think she’s the ‘what if’?”
Mary’s eyes flick toward the closed door, a smile rising. “Oh, I know she is. She always has been. And I think it’s a sign that she came back when she did.”
You shove the door open with more force than intended, the warm, suffocating cacophony of dinner and wine and laughter spilling out behind you. The night air is a relief – cool and quiet, a world away from the crushing weight of everything you found out tonight. It smells like barbecue smoke and summer grass, but it might as well be a graveyard out here with the way your heart feels.
“Hey, wait!”
Dean. Of course.
His deep voice cuts through the stillness behind you, laced with desperation. You stubbornly keep walking down the steps, but you hear his boots on the porch, then on the gravel. He’s following, and you fight the urge to lunge at him and fucking strangle him.
“Can we just–… can we talk, please?”
You stop at the edge of the yard, your hands trembling. You take a deep breath before you turn around and finally look at him. Your eyes are glassy, red-rimmed, and filled with so much hurt he physically flinches. You laugh, quiet and bitter.
“What for, huh?” you ask, your voice hollow. “Haven’t you fucking done enough?”
Dean catches up beside you, breath uneven. “I was gonna tell you,” he mutters, voice hoarse.
You let out a sharp, humorless laugh. “Yeah? When? After dessert?” You take a step closer, seething with anger and hurt from every pore. “You knew. You fucking knew exactly what you were doing last night. Don’t pretend this was some innocent trip down memory lane.”
“I didn’t plan for any of that to happen,” he says quickly. “I was just–… I don’t know, I thought we were just catching up.”
“Catching up?” you echo, fury threading through every word. “That’s what you’re fucking going with? Don’t you dare rewrite what happened between us to make yourself feel better. That night, what we shared, that wasn’t just catching up, and you know it.”
Dean shifts, uncomfortable under your gaze, shoving hands into his pockets. “It wasn’t like that.”
“Then tell me what it was like,” you prompt sternly. “Because from where I’m standing, it looked a hell of a lot like you were leading me on. Letting me believe that maybe, after all this time, there was still something here. That it fucking meant something!”
Dean’s jaw clenches. “It wasn’t–… I didn’t mean to hurt you.”
“Well, congratulations, but you did,” you snap. “You fucking did. You broke my heart all over again.”
He winces. “It wasn’t supposed to go that far.”
“No, it wasn’t supposed to go anywhere at all!” you yell, your voice cracking. “But you let it. You let me say all those things. You let me feel all of it again. We fucking kissed, for crying out loud!”
“Can you keep your voice down a little?” His eyes flick back toward the house, panic gleaming in the devastating green.
You scoff in disbelief. “What? Don’t want your fiancée to hear us? Don’t want your family to find out what a fucking piece of shit you are, huh?”
He swallows hard and mutters, “You kissed me first.”
You shake your head, taking a trembling breath. “And you kissed me back! You didn’t stop me. You didn’t even hesitate. You looked at me like you used to, so don’t stand here and act like I fucking imagined it. And all this time, you didn’t even once think to mention you were fucking engaged?!”
“I didn’t know how,” Dean argues quietly.
“That’s such bullshit!” You take another forceful step toward him, eyes burning. “You didn’t want to. Because if you said it out loud, it would’ve probably ruined the little fantasy you were clinging to. So what was I? Just an impulse? A flash of nostalgia? A little fun before you put a goddamn ring on someone else?”
He looks away, jaw tight, but you don’t let up.
“You know what the worst part is?” you whisper, fighting back the tears in your eyes. “I came back here thinking maybe I could finally be brave. That maybe if I said what I didn’t say ten years ago, if I was honest this time, it would matter. I meant what I said last night, you know? All of it. I thought maybe the world made sense again for a second. And I thought you felt that too. It felt like... God, it felt like we still knew each other. Like maybe everything we used to have wasn’t just something we left behind. And I thought... maybe we could fix it this time, you know? Maybe we deserved a second chance.”
Dean looks away again, jaw locked tight.
“But guess I’m the fucking idiot for believing that, huh?” you add with a hollow smile.
“Don’t say that,” he says quickly. “You’re not–”
“No? Then what the hell am I, Dean?” Your voice rises, chest heaving. “You let me fucking believe that maybe you still cared. That I wasn’t the only one who never moved on. I know I changed, okay? But I still thought that you’d still be you.”
Dean meets your eyes at that, and it nearly breaks you how wrecked he looks. But you don’t stop.
“But you’re not him. Not even close,” you bite. “The old you? He was kind. He was honest. And he sure as hell wouldn’t have done this. He never would’ve let me walk into that dinner without knowing. He never would’ve kissed me like that with someone else waiting at home. You used to be the person I trusted most in the world.” You stare at him, furious and broken and so unbelievably tired. Your tears begin to spill, but you don’t care. “But you? I don’t even recognize who you are anymore. You’re not the man I used to know. You’re a fucking coward, Dean.”
Dean doesn’t speak. He closes his eyes as if he can’t bear it. Like if he shuts them hard enough, he can erase it.
“I’m sorry,” he says, barely audible.
You laugh bitterly. “Sorry? That’s what you’ve got?” You wipe your tears from your cheeks with your sleeve. “I’m not angry that you’re getting married, by the way. This isn’t jealousy. I’m angry that you didn’t have the decency to fucking tell me. That you stood there, watched me walk into your home, into your family dinner, and didn’t say a goddamn thing. You let me sit next to your mother and brother like nothing was wrong. Like I wasn’t about to get sucker punched a second later.”
His face contorts like the words gut him, but it’s too late.
“I trusted you,” you continue. “Even after everything. I thought–... I thought the Dean I knew would never do something like this.” Your voice breaks, thick with devastation. “I’m fucking done with this town. With coming back and pretending it still feels like home. I thought you were the only thing left here worth holding onto… But you’re not.”
Dean’s head snaps up. He looks like he’s about to fall apart.
“I hope she gives you the life you think you want, and I hope it makes you happy,” you say coldly and force a brittle smile. “Congrats. You finally got your wish. I’m never fucking coming back here again. Good luck with the rest of your apple pie life, Dean.”
Dean’s jaw twitches. He looks like he wants to say something, anything, to fix it. But there’s nothing left to fix.
You then leave him standing there – frozen, silent, destroyed – as the night swallows you whole.
▶️ Chapter 5: Old Habits
Soooo, kids... How are we holding up, huh? 😅 I know a lot of you already suspected he had someone in his life, but did y'all think he was engaged and a week away from a wedding? 🙈 What did you think of Mary's scheming? I hinted a little in that conversation with John that there might be more to the engagement story, so hang in there. More answers and insights coming in the next part!
Now, before you all yell at me, let me remind you that I feed off screams and bathe in tears. Alright, go! 😜
Coming Up:
You sigh deeply and wish for more tequila. But you know Pamela won’t give you more. Not after you stole the fucking fish last night.
“I don’t get it,” you say after a moment. “Why would he do any of this? He took me on this whole crazy adventure last night. We went to all our old haunts. We kissed.”
“You kissed?!” Cas echoes a little louder.
“Who kissed?”
You recognize the voice behind you in an instant – Charlie. And as you glance over your shoulder, you see the others too – Benny, Sam, and Jess. It’s like time rewinds ten years, seeing all of them together again like you accidentally stumbled back into the friend group you used to be a part of.
But they all came for you.
“What the hell is this?” you ask, stunned.
Benny throws an arm around your shoulder. “What? You thought we’d leave you to drink your feelings away in solitude? You’re still one of us, chère.”
“I called in the cavalry,” Cas tells you with a wink. “Figured you could use some friends.”
Damn it Wayne I knew you was going to make me yell at you soon! Here we are where I yell at you then Dean!
I got worried for a moment like he didn’t want her to see someone. But then it was Mary and then I went whew. But the way he was trying to get Mary to not invite her in seemed off. Then at dinner it gets dropped DEAN IS GETTING MARRIED! Why Dean why lead us on?! Bad Dean bad! Mary bless her momma heart she knows Dean is making a mistake but she isn’t saying it out right. The way she is playing match maker is sneaky and I love it!
Dean needed to hear everything she said to him cause it was the truth! Dean knew better he knew what he was doing! It’s why I say Dean you..
He better fix it and fix it soon! She wanted to be with him and he acted like a coward! I know he hated hearing it but it’s true!!
Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x Reader
Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, 100% a romcom (Wayne's Version 😜), drinking & everything that comes with a crazy night out, stupid decisions like drunk driving, mentions of break-ups, fluff, angst and hurt and a rough ending
Word Count: 3.6k
Posted on Patreon April 16, 2025
A/N: Enjoy this little rollercoaster of emotion. This is just the beginning! 🤪🎢
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Chapter 3: Old Sparks
Dean said one more stop, but his actions spoke differently. As soon as the two of you were on the road again, he convinced you to go to Rocky’s for a nightcap before your last stop.
That nightcap turned out to be your downfall.
You and Dean emptied shot after shot, playing pool and darts before you told him to bolt as soon as you’d returned from the restroom with that godawful, stuffed singing trout, which held a sign that read: “Drink like a fish.”
Both of you had always hated the damn thing, so stealing it and bringing it to its final demise by drowning it in the river out back seemed like an appropriate and necessary action after ten years. You and Dean laughed, squealed and giggled as you raced down the quiet streets of Lawrence like the two of you were teenagers, running from Sheriff Mills all over again.
Fortunately, no law enforcement came after you this time, but that didn’t stop either of you from more shenanigans.
After your escape, Dean headed straight to the drive-in theater, where you caught the last thirty minutes of the midnight showing of All Saints’ Day 4: Hatched Man Lives, which just so happens to be Dean’s favorite horror flick of all time. You’d watched it every Halloween with him.
You stuff yourselves full with popcorn, nachos, licorice, Skittles and gummies before the two of you hit the road again when the movie rolls its end credits. Junk food, booze, junk food, booze – it’s a cycle you and Dean repeat throughout the day and night as you carry on with your adventure.
Suddenly, Dean then haphazardly pulls over at the side of a quiet stretch of road near an empty field a little outside of town, and you recognize the familiar land as the old Tran farm.
“Dean, what are we doing here?” you ask a little too giggly and feel like a schoolgirl again as you arch a brow at your tour guide’s mischievous smirk.
Dean’s palms drum against the steering wheel to AC/DC’s Back in Black, the excitement and adrenaline visibly rushing through his veins. “I think tonight’s the night, sweetheart,” he tells you, drunk with liquid courage and a big wolfish grin.
“Dean, no!” You wheezed, your contracting abs almost breaking you in two. “You couldn’t do it when you were twenty-one. What makes you think you can do it now?”
“Hey, I’m a lot stronger now. And the cow’s older, too,” Dean argues in boozed logic.
“Is it even the same cow?”
“I don’t know, but I’m gonna tip it over,” Dean drawls with determination gleaming in his glassy green eyes.
“Dude, no!” You giggle and shake your head but still follow him all the way into the dark field. How poetic.
Needless to say, Dean couldn’t even find the cow nor see straight, neither of you even knew if the cow still existed, and by the time the two of you had decided to free the chickens from the coop instead, Mrs. Tran ran out of the house and fired a shotgun into the air.
Laughingly, Dean and you then reach the safety of Baby, hearts beating fast as you breathlessly fall back into your seats.
“Well, that was a bummer,” you note, giggling, and share a look with your partner in crime, whose grin is broader than the full moon on a clear night like tonight.
“Still fun, though, right?” Dean says, to which you agree with a vigorous nod. “Alright, can you grab the tapes from under your seat?”
“Oh, which one d’you want? Zeppelin II or IV?” you tease as you haul out the old shoebox full of cassette tapes.
“Hey, I listen to a lot more than Zeppelin, okay?”
“Anything after the 80s?”
Dean’s mouth opens and closes briefly with a lack of a clever response before he simply rummages through the box himself and fishes out a mixtape. “Remember this?”
A wide smile forms on your lips, recognizing your own handwriting on the label – Y/N’s Favorite Traxx of 1999! If you remember correctly, it opens with the Backstreet Boy’s I Want It That Way, which Dean loathes with every fiber of his mullet rock being. To be fair, so do you, but you’ve always loved annoying him more.
“No way! I can’t believe you still got it!” You beam, holding the tape between your fingers like a precious treasure.
“‘Course! You think I’d throw this away?” Dean chuckles playfully, but you grow quiet instead of laughing with him.
“Honestly? Kinda, yeah…”
Dean’s eyes flicker to you, but he apparently decides not to get into it and keep the atmosphere light. “Well, uh, put it in,” he encourages you.
By now, the night is spilling over into the quiet hours of the morning, and you grow unsure if you want to continue this trip down memory lane, your mind starting to spin out of control with what-ifs. What does it all mean? Why is he doing this with you? He never directly makes a move on you, but the two of you avoid talking about your past relationship as well, so what the fuck are you doing here exactly?
“Oh, I don’t know. Not really in a 90s mood right now,” you reply, your gaze drifting out the window.
“Everything alright with you?” Dean checks, his eyes searching for yours in the dimly lit car, but you don’t meet them.
“Yeah, yeah,” you assure, head resting in your palm. “Just getting tired, you know?”
“Well, uh, you still up for our last stop, sweetheart?” Dean asks, his voice still light, but there’s an undercurrent filled with tension slumbering underneath it. When you open your mouth to tell him you think it’s better if you went home now, he adds a “please” and a puppy dog look.
“Sure,” you cave at last and force a weak smile. “Last one, alright?”
Dean nods quietly, and you notice the soft creases appearing on his brow that tell you he’s not liking the sudden shift in the air between you. Nevertheless, he still pops in your cassette tape, the Impala’s silence filling with the Backstreet Boys, as if Dean doesn’t want to let go of the past either.
Baby comes to a stop at the edge of a cliff, a few town lights that are still on twinkling below you like little stars. Dean’s last stop is Heaven's Lookout – the local teen make-out site and a place where you’d spent countless hours entangled with him.
In fact, you’ve lost your virginity in this exact spot in the backseat of the Impala.
The nightly summer air is cool and crisp as the two of you settle into a comfortable and easy silence on the hood of the car, facing the horizon. For a heartbeat, you just breathe and enjoy the view, side by side. When you steal a glance at the backseat, Dean catches you and chuckles softly.
“What?” You arch an eyebrow.
“Nothing.” He laughs lightly, shaking his head. “I guess I just know where your mind went now. We’ve had some good times here, didn’t we?”
“Yeah, I guess so,” you agree quietly, but it’s not the reaction he’s hoped for.
“You guess so?” Dean cocks his brow at you and playfully nudges you with his shoulder, seeing the faint hints of tears brimming in the corners of your eyes. “Alright, what’s going on with you?”
“I told you. ‘M just tired,” you lie once more.
“Hmm,” Dean hums, not believing you even for a second. Ten years might have passed and both of you changed slightly, but he still knows you too well – better than anyone on this planet. What a fucking heartbreaking thing to realize. “C’mon, talk to me, sweetheart.”
“Not in the mood to talk, Dean. Just leave it be,” you reply and keep your focus on the twinkling town lights, trying to keep the tears at bay.
Have you ruined your life by leaving ten years ago?
“Alright, how about I start, huh?” You only offer him a careless shrug as a response, and Dean exhales a small sigh. He swallows thickly, his gaze fixed on his hands in his lap. “I lied to you earlier… in the diner,” he starts, and you meet his eyes with a tilt of your head then.
“About what?”
“I did read your books. Multiple times, actually. Pretty sure I can even quote every line by now,” Dean confesses with a self-conscious chuckle.
“Oh.” You honestly have no idea what to say to that. You don’t even know how you feel about it. Are you happy? Sad? Feeling exposed? Horrified? Probably a bit of everything. “Why did you lie about it?”
Dean scratches the back of his neck. “Well, uh, to be quite frank with you, I kinda resented your entire industry for a long time for taking you from me, you know?”
“I’m really sorry how things ended between us,” you tell him, licking your lips as you search for the right words. There are still things he doesn’t know, that no one really knows, and you decide it’s time you finally unburden yourself from some of them. “I just-… Remember when I really wanted to go to Brown?”
“Yeah, I do. When you got that rejection letter, I even took you here to cheer you up. We ate ice cream, and, uhm, I told you if they didn’t want you, it was their loss and you’d find something else. And you did. You went to KU. I mean, it’s not Ivy League, but at least you got to go with Cas, Meg, and Charlie, right?”
“Yeah, uhm, I might have lied about it back then,” you confess, eyes fixed on him. His brow knits, confusion flashing across his freckled face. “Brown did accept me, I just chose to stay here with you.”
Dean’s mouth is agape as your revelation sinks in. “Why wouldn’t you have said something?”
You give him a twitch of your shoulders, small and reluctant. “I didn’t wanna leave you,” you admit, your fingers fidgeting in your lap. “But I did wonder, you know? What would’ve happened if I’d gone… So, when that publisher was interested in my manuscript and told me I had better chances if I moved to New York, I felt like I finally had to shoot my shot, you know?”
“Yeah, uhm, I know. I get it.” Dean’s raspy voice softens, his mind racing a mile a minute. “Look, I’m-… I’m sorry for being such a dick to you back then. You didn’t deserve that. You tried, and I didn’t let you. I know I wasn’t being fair to you. I was just scared to lose you. I knew I would eventually if you went to New York, you know? Like you’d realize then that there’s better things out there than me. Guess I thought if I ripped the bandaid off quickly right then, it’d hurt less than later down the road. But I was wrong about that, too… I still was always proud of you, though. Never had a doubt in my mind that you wouldn’t make it. You were meant for great things, y’know?”
You close your eyes because if you don’t, the tears would fall freely. Somehow, hearing everything you ever wanted to hear over the last decade only hurts more than it heals. And you know why, as those same old regrets settle in your heart.
“I wanted to be with you for the rest of my life. You were everything to me,” you whisper and almost choke on the words, the first tear slipping down your cheek.
“Yeah, I know that now.” Dean’s eyes glisten like lush green moss under rain, a chuckle devoid of humor leaving him. He doesn’t look at you, and you don’t look at him, both of you lost in the town you grew up in, sprawling out below your feet. “Feeling’s mutual, sweetheart.”
“But you still broke my fucking heart.”
Your voice carries sadness, torment carved into its edges. It’s the kind of pain one only wins by losing a first love. It’s not meant to sound reproachful. It really isn’t. It’s just one of those tragic facts of life that neither of you can deny.
Dean nods, lips drawing into a painful smile. “I know,” he rasps quietly but still doesn’t dare facing you, as if the smallest glimpse at you could shatter his heart. He’s not strong enough to take it. Not as strong as you, at least. “You never told them the truth. About what happened. Benny, Cas… Not even Charlie and Meg. Why? I mean, you could’ve had it so easy, making me look like the asshole because I was. Instead, you just went with my narrative and never looked back. I never understood why.”
Your head bobs in thought. “I guess I didn’t want to hate you. And I didn’t want them to hate you either. You just seemed like you needed them more than I did back then, and I’m fine with being called a bitch, so…” You offer him a half-hearted shrug and sniffle more than you smile.
Dean expels a breath of disbelief, and you don’t entirely know what it’s about. Maybe relief he finally got an answer to a long-pondered question? Or maybe it's because he never truly thought you could be so selfless, considering how he’d ultimately deemed your decision as selfish.
And maybe, just maybe, it might be the shock of realizing you’ve still chosen to protect him, even after everything he’s put you through.
“You know, you asked me today why I barely ever come home, and I think you should know that the reason why I don’t is you,” you share and can’t keep the bitterness from slipping into your syllables. And for the first time in ten years, you realize just how much you’ve resented him for what he’s done to you. “It’s not that I never wanted to look back. You told me not to come back. Remember that one, too?” Your words aren’t bitter anymore but brackish. “I always planned on coming home once my first book tour was finished. I didn’t wanna leave forever. My life’s not exactly that great, you know? I’m not that happy. The last time I was happy was when I was still with you.” The rawness of your words rattles him, his face softening. “And I don’t know… After everything, I didn’t really think I could come back. You closed that door, not me.”
“Yeah, I know…” Dean nods, wiping the tears from his eyes. His hands are shaking as he rubs his mouth, fighting to push back the wave of regret. “I realized pretty early on that letting you go was a big fucking mistake. I-, uhm, I actually flew to New York six months after you left. Came to your launch party at that fancy bookstore when your first book came out.”
Bewildered, your mouth falls open, shaking your reeling head. “I-I didn’t even know you were there. I didn’t see you–“
“No, I know,” Dean cuts in. “I came there to get you back, try to convince you to leave with me and come home. But when I saw you, I realized that was wrong. I mean, all your dreams were coming true. You looked happy. I didn’t wanna be the guy that tore you away from that. Didn’t exactly have a lot to offer you back then.”
“You had plenty in my eyes.” You send him a soft smile, its tenderness surprising even you.
Dean swallows hard, throat tightening with every heavy breath. “I still kept thinking about you. Never really stopped…” His admission hangs between you for a moment. “And, uhm, when we opened our second location and business was going good, I figured that’s something, you know? So, three years after New York, I decided to try again when I heard you’d be in Kansas City during your book tour, but, uhm, I guess you’d already started dating that hockey player then…”
“Right…”
A rueful smile plays across his lips. “You know, I’d be lying if I said I don’t still think about what would’ve happened if you’d stayed all those years ago… or if I’d just gone with you.”
“Yeah, I’ve been wondering about that, too. All the damn time, actually,” you say, locking eyes with him. “Maybe leaving was the wrong decision…”
Dean goes silent for a moment, a spark of hope igniting on his freckle-dusted face. His eyes search yours, as if trying to find a treasure he’s lost years ago. “You really mean that?”
You nod and lean in slowly, gauging his reaction as your heart hammers wildly in your chest. The chasm between you two closes.
Dean doesn’t move or pull back, not even when your hand reaches out and tenderly caresses his cheek, the scruff surprisingly soft under your fingertips. His eyes close, Adam’s apple bobbing with a light swallow. He gives in to your touch, and with a breathless exhale, you press your lips on his.
It’s tentative at first, a question in form of a brush, painting with water and not color. Transparent on canvas.
The kiss only lasts a second or two before you pull back but never go far. You seal air in your lungs and wait, giving him a chance to bail if he wanted to.
But he doesn’t. He draws you right back to him.
Dean brings the vibrancy to your blank page, his colors spreading across the canvas and crowning it art. Your lips part against his, let him claim you as his tongue slips inside and meets yours. Years of separation, of regret, and of longing burst through the lines.
Raw. Hungry.
Dean’s hands grab hold of your waist, pulling you closer, short of dragging you into his lap. His kiss grows more urgent – like he’s trying to make up for lost time. It’s frantically ardent and boldly desperate. And mostly, it’s full of everything you’ve both kept buried for far too long.
It’s not like any kiss you’ve ever shared. It’s different. Better. Because you finally know where you belong.
Here. With him.
His hands roam, explore familiar territory anew. His fingers trace your pulse point, feeling your heart’s rapid beats underneath his pads. You gasp for air, swollen lips wandering down the column of his throat. His skin tastes salty on your tongue, a low groan of defeat rumbling in his chest as he succumbs to you.
“What d’you say we make the backseat the last stop on memory lane?” you whisper with a suggestive smile, hands cupping his neck as you nudge his nose with the tip of yours. You haven’t left a mark on his skin yet, but you surely plan to make him yours again.
But hesitation creeps into his expression. His lips part in contemplation as he looks at you, your labored breaths mingling in the fresh, early morning air.
“What?” you check with a bemused smile, hiding caution behind it. You know that look of his and don’t like the heavy weight pressing down on your heart, the sheer force threatening to crush it.
“I-, uh, I think maybe we should call it a night, y’know?” Dean says and gently puts his hands on your arms around his neck, loosening their grasp on him.
Holy fucking shit.
The embarrassment floods your senses, every word of his adding a new crack to your heart. No one gives you whiplash quite like Dean Winchester.
Your hands flinch back and let go of him, the rejection seeping into your bones. You shake off the stupidity and bring distance between you two, jumping up from your spot on the hood.
“Oh, yeah, no, you’re right,” you agree in a silly attempt to save face – not that Dean can’t see right through it, but at least you can forever pretend you both came to that same conclusion.
Dean wrings for words, witnessing the hurt shimmering in your eyes. It almost forces him to come closer again and pull you into his arms, but he’s trying to keep his head on his shoulders. He’s already messed up enough for one night.
“It’s just-… You’re only in town for a few days,” he argues softly. “I wouldn’t want to get too–“
“No, no, totally. I get it. No worries,” you assure him with that little bit of pride that’s still there. “I’m gonna walk home, okay? Thanks, uh, for everything. I had a great night. I really did. Was good to see you again and catch up, Dean.” You send him a smile and act like the tears aren’t blurring your vision.
“Y/N, wait! At least let me drive you home,” Dean offers, his heart pulverizing at the crestfallen sight of you. He’s promised himself he’d never hurt you again. How has he ended up here?
“No, really, I’m fine,” you assure him, holding up a palm to stop him from following you. “Not the first time I walked home from here. It’s not that far. Sun’s already coming up. It’s the perfect way to end memory lane if you think about it,” you add and force a weak smile, sniffling. “Take care, okay?”
Dean nods with a hard lump lodged in his throat but doesn’t say anything more, watching you disappear from his life again.
▶️ Chapter 4: Old Scars
You guys ready to murder me yet? 😂 And yes, this is where the angst comes fully in. But don't worry – I made it funny too, so you never know if you'll be sniffling or snorting 😘
Coming Up:
“Oh, Y/N… Hey.” Dean’s brow shoots up once he recognizes you.
Your heart stops abruptly. He doesn’t seem happy to see you. There’s no smile on his plump lips, only panic in his green eyes. It’s not a good sign that necessarily boosts your confidence.
Neither is the fact that he quickly steps out onto the porch and shoves the door almost entirely shut behind him, only leaving an inch of leeway. While he doesn’t say it directly, he’s surely not planning on inviting you into his home.
He has also called you by your name instead of the endearing “sweetheart.”
Fuck. Maybe this is another bad idea of yours. He’s clearly not thrilled about your visit.
“Hi, uhm–,” you finally manage to spit out and offer a tentative smile, your fingers fidgeting with the sleeves of your old jeans jacket. “Look, I would’ve texted you that I was coming by, but I don’t have your number anymore, so…”
We are starting off funny here! Omg not the stealing of the fish!! 😂 Honestly I probably would have done the same. Dean trying to push a cow is hilarious! You really can’t push them over they look like they would fall over but they won’t. Also freeing the chickens had me laughing and going FREEDOM FOR THE CHICKENS! 😂
OMG I KNEW IT! Dean really did read her books I knew it!!! But come on Dean what are you doing here! The way she poured her soul out to him looking for a way to reconnect had me in awe. But there is something Dean isn’t telling her I just feel it. That kiss though whew!! Then she basically throws herself at him wanting to try again and he rejects it! Why Dean why?! Dean doing that had me like
I have a feeling I will be yelling soon! But love this series so far.
Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x Reader
Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, tiny bit of angst, fluff, 100% a romcom (Wayne's Version 😜), drinking & everything that comes with a crazy night out
Word Count: 5.3k
Posted on Patreon April 9, 2025
A/N: Welcome back! June did us dirty, and I'm still catching up on everything, so expect a post dump with all your sweet comments coming in soon. But without further ado, here's some fluffy, drunk-in-love reunion and glimpses into their past 😉
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Chapter 2: Old Haunts
“Wow, I haven’t been in here forever,” you say as Dean leads you into Bobby’s Junkyard – Lawrence’s go-to diner for young and old alike.
Dean and you used to come here almost every day for burgers and milkshakes during your youth. The warm, nostalgic hum of the place instantly wraps around you like an old, favorite sweater you’d found under your twin bed.
But it’s also where you told Dean you were going to New York – whether he liked it or not. Considering this, you find it quite odd he’d bring you here first.
It surely isn’t the best memory for you, but judging by his happy grin, you know he clearly isn’t thinking about that night. He’s remembering all the good times you’ve had here, all the laughs and conversations, and you can’t help but recall them, too.
“Figured,” Dean says and casually rests a palm on the small of your back, guiding you to your old booth.
The red vinyl seats creak with familiarity as you settle in across from him, painfully aware how much time has passed since you last sat in that same spot. His green eyes even still hold the same warmth that always made you feel like home.
You honestly can’t quite believe he remembers all of this. After everything that happened between you two, you’d been dead sure he’d incinerated every memory he ever had of you. You wouldn’t even have blamed him if that had been the case.
“What are you doing?” Dean tuts and quirks a brow at the laminated menu in your hands.
“Seeing what I can order. I have a friend from Barre class who got me onto this whole Paleo diet thing,” you say mindlessly as your eyes skim the options before the menu is snatched from your grasp. “Hey!”
“None of that fancy New York shit here,” Dean says and tosses the menu on the unoccupied table behind him. He eyes you with a scrutinizing look. “Don’t insult our tradition.”
“Dean…” You sigh and roll your eyes, hearing his amused chuckle at your protest. “Do you know how long it’s been since I ate that much fat and sugar?”
Dean grins lazily. “I’m guessin’ too fucking long, sweetheart. You’re gonna commit to memory lane or not? Sin a little with me, huh?”
“Fine,” you relent, smiling. Who could say no to that? Your gaze then wanders up when your waiter comes to your table, your smile and eyes widening with both surprise and delight. “Oh my God, Benny?!”
“Well, if it isn’t Lawrence’s lost daughter,” Benny greets you with a broad grin. “Look at you, chère! Only gotten prettier in the last ten years.”
“Oh, stop!” Giggling, you shake your head and get up to hug him before settling back into your seat. “How have you been? I can’t believe you still work here,” you say before realizing how incredibly condescending that sounds, quickly correcting course. “I mean, not that there’s anything wrong with that. No offense.”
Amused, Dean snorts at your blunder. “Smooth.”
Luckily, Benny only barks a loud laugh and doesn’t take your comment to heart. “Still the same spitfire, I see.”
“You know, Benny actually bought this place from Bobby three years ago,” Dean tells you, sending his friend a smile full of pride.
Your heart stings a little again, as if someone was rubbing salt into an old wound. Dean, Benny and Cas had all been best friends, and for as long as you’d dated Dean, you’d always been hanging out with them and the girls, too. You’d all been friends once, but after the break-up, you felt booted out of the group – not that they’d ever officially declared a ban, but you knew where their alliances lay.
Moreover, you didn’t think you deserved them after leaving like you did.
When your first book was published, you didn’t even invite them to the launch party, fearing they wouldn’t show up anyway. Truthfully, you’d cried all night because you would’ve wanted no one rather there than your friends – and Dean. It’s the night you realized you’d be on your own from then on out.
“Wow! That’s awesome! Congrats, Benny,” you say with a genuine smile. It seems like everyone in your hometown is doing well and has found their place. But what about you? You can’t help but feel more lost than ever before.
What do you have to show for yourself? Three bestsellers? Great! What else? An empty apartment? Expensive wine? Do you even have friends you actually like? And Hemingway doesn’t count. Most days, you’re not even sure he likes you all that much, either. And what about dating? Your last long-term relationship ended four years ago. Your dating prospects have been more than lousy since.
“My, thank you. Old man didn’t have any kids, you know? And like you gracefully pointed out, chère, I have been working here for a long ass time,” Benny says with a teasing grin.
“Alright, I’m sorry, okay?” You laugh bashfully, your cheeks rosier than the glow of a ripe peach. “But hey, I’ve heard you’re doing well in the dating department, too. You and Donna? I’m so happy for you guys! Great choice, man. I always thought Andrea was a bitch.”
Dean and Benny both burst into laughter at your blunt honesty. You’ve always been a bit of a shit-starter in the group. A lot of bar fights at Rocky’s began with your words: “Oh, yeah? Wanna say that again to my friends over there? They’re gonna beat you the fuck up, buddy!”
“Now, where did you hear that, chère?” Benny asks puckishly, his eyes drifting to Dean opposite you.
“Oh, uh, actually Charlie told me. You know word travels fast in a small town. She’s been keeping me in the loop over the years,” you tell him and notice Dean straighten at that information in the corner of your eye.
“Shoulda known. That girl can’t keep anything to herself.” Benny chuckles, shaking his head. “What about you, huh? Still seeing that NHL player?”
“Oh God, no!” You snort at the reminder, vividly shaking your head. “No, we broke up a long time ago. Thankfully.”
“Well, good. His team sucked,” Benny quips. “So, what can I get you guys? The usual?”
“Yup.” Dean nods and snips a finger at you with a click of his tongue. “With extra bacon, cheese, and fries for her. Oh, and, uh, add another slice of pie as well.”
“I hate you,” you reply with a playful glare at Dean, but your cheeks are hurting from smiling too goddamn much. For the first time in a decade, you start to feel like you again. It feels like home – in the best possible way.
“Do you really?” Dean returns with an awfully flirtatious and bold smirk.
“Alright, usual with extra junk coming right up,” Benny cuts into the heated moment and clears his throat. “Hey, uh, Dean? You have a minute to look at my truck out back again? For some reason, the damn thing wouldn’t properly start this morning. Givin’ me a lotta trouble…”
Dean purses his lips and folds his hands on the table, and you can tell by the look the two men share, their silent conversation surely isn’t about the car. It’s about you, Benny probably wanting to warn his friend about the dangers of hanging out with an ex. And a small part of you wholeheartedly agrees with him.
It’s only been two hours since you’ve entered Dean’s orbit, but all those feelings you’ve kept buried underneath the surface begin to dig themselves out of their grave. You can’t help but wonder if Dean feels them coming alive, too.
Maybe there’s still something there, an old spark that could grow into a flame – or a wildfire that burns everything down.
You won’t know until you dare to find out.
“Uh, kinda have taken the day off and catching up here. Just call Garth at the shop to check it out,” Dean tells him with a polite ‘fuck off’ smile.
Benny gives a reluctant nod and forms the same defiant expression on his face. “Alright, brother. Your choice.” With a defeated sigh, he then beelines for the kitchen.
“So, Charlie’s been giving you updates, huh?” is the first thing Dean asks when Benny’s out of earshot, causing you to wonder what his curiosity is truly about. Why does he care? After your harsh goodbyes, you didn’t think he ever wanted to hear from you again.
“Yeah, she’s been sending me very detailed newsletters over the years.” You chuckle lightly and try to deflect. “I honestly think she could be a writer by the colorful language she uses.”
“Huh, yeah, she’s-, uh, she’s hoot,” Dean says with a tight smile, scratching the back of his neck. “So, uh, what d’she say about me?”
“Oh, uh…” You stump a little at his direct approach but decide to go with honesty. “She-, uh, she actually never mentions you. And I don’t really… ask, you know?”
“Right, yeah, no… That makes sense,” Dean replies and awkwardly clears his throat. Is he actually hurt by that or relieved? You can’t really tell but find his reaction odd, nonetheless.
And then, until your food arrives, the two of you stick to small talk about Benny and his plans for the diner, catch up about Bobby, and talk a little more about the Winchester clan – John’s health issues and Sam’s blooming law practice in Palo Alto.
“Fuck me,” you moan with a mouthful once you’ve taken the first bite of your burger and instantly wash it down with a big gulp of strawberry milkshake. “God, this is so good! I honestly forgot how fucking awesome this tastes.” You then notice Dean’s enchanted stare and arch a brow, giggling. “What?”
Dean shakes his head out of his stupor, swallowing. “Uh, nothing. Just happy you’re finally enjoying food again and eating a real meal instead of all that big city crap, sweetheart. What the fuck is a Paleo anyway?”
You snort a laugh. “Bunch of big city bullshit, I guess.”
“Hm. Exactly what I thought.” Dean’s lips rise to a pleased grin at your response. “And what about that bar thingy, huh? You becoming a lawyer like Sammy now, too?”
“No.” You laugh again. “It’s this new workout trend. Kinda a mix of yoga, Pilates, and ballet.”
“Fancy,” Dean teases with a mock posh expression. “You wearing a tutu for this?”
You lean forward with a bit of a daring look in your eyes. “No, actually, it’s more like a black, skin-tight bodysuit kind of thing,” you explain casually and watch his Adam’s apple bob in triumph.
“Uh-huh, think I get the picture…” Dean mutters and stuffs his dry mouth with a bite of burger, but you notice how his eyes escape down your frame.
“So, did you ever read any of my books?” you ask after a small pause but hide your genuine curiosity behind casualness.
For years, you’ve wondered if he ever had and recognized himself in your words. The stories in your books are echoes of your shared past, and while it isn’t exactly obvious to a stranger, Dean would probably recognize himself on every page.
Dean, on the other hand, seems a bit taken aback, suddenly squirming in his seat, his green eyes looking everywhere near you but never directly at you. “Uh, no, actually. Sorry,” he replies and occupies his lips briefly with a sip of milkshake. “Always wanted to, you know? Just never got around to it. Life kinda got busy after you left. You know, with the business and my dad…”
A part of you feels relieved. How embarrassing would this reunion between you two have been, otherwise? But another, bigger part of you is mad he never bothered. For the first few months after your move to the city, you’d always hoped he’d come for you, fight for you, but he never did. Maybe if he’d read what you had to say, he would’ve.
“Dean, it’s fine. You don’t have to give me an excuse. I don’t care either way. Was just curious, you know?” You shrug your disappointment off with nonchalance and hope he doesn’t see right through it. “They’re just a bunch of fictional crap, anyways. Still surprised they even became bestsellers in the first place.”
Dean’s brow furrows, and you know by the quirk of his lips that he’s seconds away from trying to cheer you up and convince you of the opposite. You know because he’s always done that whenever you’ve put yourself down in the past, only now you don’t feel he has any right to, his sheer attempt even angering you more.
“What, no, c’mon! Your writing has always been amazing! I’m not surprised someone else saw that you’re phenomenal, too. I always told you you’d make it,” Dean showers you with flattery, but it’s hard to believe at this moment. “I’m sure your next book will be a bestseller, too. You’re unstoppable, sweetheart.”
You purse your lips, your gaze musingly fixed on the two leftover fries on your plate before you meet his eyes. “How would you know, huh? You didn’t even read the first three,” you snip and watch his tongue poke the inside of his cheeks as he takes in your comment.
But there’s really no reason for animosity after ten years. Does it really matter what your ex from high school thinks?
“Look, uhm, I’m sorry. Maybe this was a bad idea. I should probably go now, spend some time with my mom…” you say and rise from your seat, opting to take the high road. You put down enough money to cover both your orders and include a generous tip for Benny. “Thanks for indulging me, though. It was nice catching up with you again, Dean. Take care, alright?”
Sure, you could have said lot of things. The two of could’ve even screamed your lungs out at each other. You never felt like you’d gotten the infamous closure. You’re not even sure you understand fully why you broke up in the first place. It all imploded so quickly back then. But why would you want to know now? What good could it do? The past remains the past. Opening old wounds and fighting ancient battles seems like a useless waste of time.
“Y/N, wait! Don’t go!” Dean’s hand grasps your wrist and pulls you back before your feet reach the exit. You meet his gaze, his hand loosening its grip and drifting to your palm, your fingers brushing before he lets go entirely. “Look, uh, I’m sorry.”
You smile a little, your features softening. “What exactly are you sorry for?”
“Well, uhm…” Dean scratches the back of his head. “Not exactly sure, quite frankly, but I know something I said upset you. Guess that hasn’t changed either.” He chuckles self-consciously.
“No, uh, you didn’t upset me, Dean,” you lie and offer him a soft smile that’s supposed to hide your true feelings. “Just remembered why this isn’t a good idea, you know?”
“Alright, hold on, okay? Maybe you’re right, but at least gimme one last shot to prove you wrong, sweetheart. What d’you say?” Dean’s smile is so charming and inviting it seems like an impossibility to deny him anything.
Matching his smile, you cave with a little sigh. “Go ahead. Shoot your shot, Winchester.”
“Okay, stay here. Don’t you dare move.” Dean grins victoriously and rushes past you to the far end of the diner, and it suddenly dawns on you what his plan is.
On cue, the diner fills with music from Bobby’s old jukebox, playing a song Dean just picked. You recognize it immediately and send him a raised look, partially amused by his choice as Can’t Fight this Feeling starts.
“Really? REO?”
“C’mon, it’s our song,” Dean argues goofily and joins you again in a few strides.
“Yeah, and like I told you back then a million times, I refuse to accept that,” you retort, laughing.
“Welp, don’t care,” Dean quips. He then holds out his palm, smirking. “Will you do me the honor and accept this dance, Ms. Y/L/N?”
You chortle but hesitantly agree to his offer, placing your hand in his before he pulls you flush against his body in one suave motion. His other hand comes to rest on your lower back while yours lands on his shoulder, feeling the dips of his muscles under your pads.
“It’s the song that played the first time I asked you to dance during our junior prom. Remember that?” Dean’s eyes find yours as you get lost in his embrace.
Goddammit, you’ve missed those arms around you. They make you feel safe and loved. They always have, and now you’re sure they always will.
“‘Course I do. My mom forced me to go to get outta the house. I so didn’t wanna be there. Not even Charlie and Meg got me out of my mood,” you recall.
“Yup, and then came me.” Dean chuckles warmly, feeling the vibrations against his chest. “I’d had my eye on you the second Cas brought Meg and her friends around, including her hot and smart friend. But you were pretty damn unapproachable, sweetheart.”
“Yeah, well, let’s just say your reputation as a heartbreaker preceded you, Winchester,” you sass.
“You were definitely a hard one to win over.” Dean laughs a little at the memory. “But when I saw you sitting there on the bleachers of the gym, reading goddamn Kafka of all things, I thought I try again, even when Benny and Cas told me to give up because you clearly ain’t interested.”
“And you did come over and surprised me by quoting a line from the book I was reading. Still remember which book it was?” you challenge him.
“Yeah, The Trial,” Dean shoots like a pistol. “Kinda made me like you more. Still remember the quote, too. ‘I like to make use of what I know.’”
You laugh, your cheeks warming. “Yes, exactly! And then you proceeded to tell me you were a great dancer and had to make use of it.”
“Worked like a charm, didn’t it?” Dean grins down at you.
“It did.” Your eyes stay connected as you sway to the music and follow Dean’s lead, aware you’re being watched by a few diner customers now. But Dean doesn’t seem to care, so neither do you and just enjoy the moment. “Still remember what happened by the end of the song?”
You kissed him, and he grinned right through it.
“Yeah,” Dean smiles softly, “Changed my whole life, sweetheart.”
You mirror his expression as your heart swells. “Yeah, mine too.”
And you can feel it then, in the air around you two – you’re catapulted right back to the moment where you fell in love. Your heart is beating exceptionally fast, and you know his is, too.
“So, uh, you’re curious what’s next on the list?” Dean interrupts the electric silence, clearing his throat before twirling you around and catching you again with a playful smile.
“Uh, I didn’t know there’d be more,” you reply and can’t help breathing in his scent as he holds you close. That one hasn’t changed either. It’s still full of pine, leather, and motor oil, but it’s even more unique and indescribable than that.
“Of course there’s more,” Dean states as if it were obvious he’d want to spend more time with you. Where will it lead, though? What’s his agenda here? He can’t possibly think this is a normal thing to do with an ex-girlfriend, who someone hasn’t seen in over a decade. “C’mon, you didn’t really think memory lane ends here, right? This is just us fueling up before the trip even starts. Didn’t want to get you drunk without ensuring you had some nice, greasy padding in your stomach.”
“You wanna get me drunk, huh?” Laughingly, you lift a brow. “So, what’s the next stop on memory lane? You takin’ me back to Rocky’s?”
Dean grins broadly. “Oh no, way better, sweetheart.”
“Fine,” you agree once more, unable to cut the invisible string that ties you to him. “But if we’re gonna do this, I have to change outta those clothes first.”
“Now, we’re talking. Can’t wait to see you outta that pantsuit,” Dean teases, smirking.
You scoff in amusement. “It’s just slacks and a blouse. This hardly passes as a suit.”
“Coulda fooled me,” Dean retorts playfully and holds open the diner door for you like a gentleman.
Dean leans against his car with crossed arms as you walk – or run – out of your mom’s house again, meeting him on the small cobblestone path that leads up to the porch.
“That was quick,” Dean notes. “Didn’t even think you could change that fast. Surely never were ready this quick when we were still dating.”
“Yeah, well, trust me, wasn’t quick enough,” you huff. No kid should hear those sounds coming out of their mother’s bedroom.
Dean’s lips rise to a grin at the realization. “Ah. And how is Connie these days?”
“Busy,” you reply and add bitterly, “With Mr. Edlund.”
Dean’s brow knits, the smirk turning to a frown of disgust. “Our high school English teacher?”
“That’s the one,” you reply in sing-song.
Dean snorts a laugh. “Guess Connie hasn’t changed a bit, huh?”
“Nope, she hasn’t,” you murmur, smacking your lips. “Probably the only person I’ve always wanted to change. Funny how that works.”
“C’mon, she ain’t so bad. I know you love her,” Dean says, gently nudging your shoulder.
“No, I do,” you admit and look at him. “I’m here, right?”
“Yeah, you are,” Dean says softly before the boyish smile reappears on his freckle-dusted face, eyeing your choice of outfit – your old jeans overalls. “Can’t believe you put on the fucking overalls.”
“Hey! I loved them, okay? ‘Sides, you said I had to commit to memory lane, so consider me committing to denim. Even wearing my old flannel, so I match with you,” you reply slyly, pinching a bit of fabric on your arm between your fingers.
“Oh, you mean my old flannel?” Dean cocks a brow, a smile tugging at his lips.
“Huh, I guess. Forgot about that...”
You feign innocence as you steal a glimpse at it. Of course you’ve known it used to be his. You certainly haven’t picked it out by accident. Going through your old closet in your childhood bedroom, you’d come to the conclusion you wanted to see where this little adventure with the former love of your life would lead.
“Also not wearing a bra, by the way. You know, for old time sake,” you add with a cheeky wink and slide into the passenger seat, reminding Dean of your past aversion of unnecessary clothing items.
You figure it can’t hurt, and by the amount of time it takes him to climb into Baby after you, it certainly hasn’t.
“Mini golf?” You lift an eyebrow as you step out of the Impala and onto the familiar pavement of the parking lot.
The course sits right next to the arcade and the bowling alley. You’ve spent countless hours here with your friends, including a few heated make-out sessions with your green-eyed companion on that very parking lot.
“Hell yeah! We haven’t played in forever. We used to come here all the time,” Dean says, chuckling, and rounds his way to the trunk, pulling out three six-packs of beer cans.
“Oh no, Dean… We’re not doing Shotgun Mini Golf,” you warn playfully once you realize his plans. “We’re way too old for this!”
“Nonsense,” Dean says and grins at you, leading you toward the entrance.
The sun hangs low in the sky, its golden rays spilling over the miniature course. The humid Kansas air clings to your skin, thick with the chirps of cicadas and the occasional clink of a ball against plastic as you position yourself in front of the first hole with your neon pink putter.
“You think you’ve still got it, sweetheart?” Dean teases with a big grin, performing his usual trash talk. “I think you’re gonna be very wasted by the time we reach the last hole.”
“Oh, you’re on, Winchester.” You grin back slyly and swing your putter with practiced ease, the ball rolling steadily across the green and sinking into the hole with a soft plunk.
“Well, shit…” Dean whistles lowly and seems to realize his chances aren’t as great as he initially surmised.
“Your turn,” you sing triumphantly as you shoulder past him and watch his next move with interest.
Dean, undeterred, steps up to his shot. He lines up the ball, takes a deep breath, and swings – but the ball veers off course, clanging against the edge of a ramp and skidding toward the side. After three strokes total, he finally gets the ball into the hole. He exhales a defeated sigh, scratching the nape of his neck.
You let out a soft laugh, loving the sight of your ex already off his game. “Enjoy!” With a wide smirk, you hold out a can of beer for him at eye level.
Dean grabs it and digs out an Army knife from his pocket, puncturing a small hole near the bottom of the can. A hiss escapes before he covers the hole with his thumb and pops open the top. And then, you watch him in amusement as he tries to keep up with the rushing stream of golden liquid, chugging the whole can as beer trickles down his chin and arms, thoroughly soiling his flannel and jeans.
“Shit!” Dean coughs as he gulps down the last drops of beer, shaking his wet and sticky hands after discarding the empty can in the nearest trash bin. “Alright, maybe this was a bad idea. Been a while since I’ve done this.”
You laugh wholeheartedly. “Uh-uh, no backsies, Losechester.”
Dean snorts at the old nickname. “Alright, sweetheart, your funeral.”
But for the next three holes, it surely was Dean’s own eulogy before your luck seemed to turn, and you lost the following four rounds. By hole twelve, both of you were toe to toe and notably drunk, tumbling over obstacles and double-visioning holes and balls.
“Call it even?” Dean asks breathlessly, resting palms on his thighs after shotgunning the last beer.
The nausea bubbling in your stomach agrees with him, and you give him a tight-lipped nod, taking his steadying hand when he supportively offers it to you. How have the two of you ever managed to finish the whole course when you were younger? It seems like an impossibility now, and maybe the thought even extends to your relationship.
You can’t just get an old thing back, can you? It’ll never be the same.
The last traces of daylight are swallowed by the dark Kansas sky, dotted with a thousand twinkling stars above as the two of you stumble out onto the parking lot, your laughter ringing out into the quiet summer night.
“I can’t believe we did this again,” you say between bursts of giggles, one hand clutching his arm as if you might collapse into him at any second.
Dean’s arm slings around your waist when you almost fall, steadying you a little more, his hot breath fanning against the shell of your ear. You laugh even harder, pressing your palm on his solid chest for balance. He feels warm against you, and although everything feels fuzzy, the old magnetic pull is undeniable.
Your glassy gazes lock, and he softly tucks a strand of hair behind your ear, his fingers lingering on your cheek a little too long. His touch and closeness send shivers up and down your spine, soon reaching that sweet spot between your thighs.
“So, what now? Is this where we call it a night?” you ask innocently, your eyes drifting down to the plump, pink flesh of his lips that cause an urge within you to sink your teeth into them. Is he still a great kisser?
You’ve surely never encountered the same magic with anyone else after him.
Dean does what you can’t and bites down on his bottom lip, his eyes musingly swerving around. “No, c’mon! It’s barely after nine! I’ve got more stops on my list.”
Your lips rise to a smirk, your heart expanding in your ribcage and almost squeezing through. “Do you now?”
“Hell, yeah! I haven’t seen you in ten years. I’m not letting you go that easy again, sweetheart,” Dean replies, not noticing the drunken honesty in his words at first, but once he does, he subtly clears his throat and takes a step back from you. “How about some fuel, huh?” He gestures to a food truck across the parking lot.
“I could eat again,” you agree but wonder what his hesitancy is about. The old him would’ve already taken his shot and kissed you. He surely had plenty of opportunities tonight, always backing out at the last second.
Does he not want this, too? And if not, why is he doing all of this and dragging you down memory lane in the first place? He certainly doesn’t seem to want the night to end, either.
With your plastered mind racing, you and Dean then settle down at the picnic table on the lot with some tacos and two pops. The night feels expansive, the parking lot stretching out into nothingness, a sea of concrete and empty space under the lights of buzzing streetlamps.
“So, how are things with your mom, really? And don’t serve me the bullshit version you give strangers,” Dean says, breaking the silence after the first few bites.
“Uh, you know, same, honestly. Like I said, Connie hasn’t changed much,” you reply, offering him a smile. Whenever you’d grown frustrated with your mother back then, you’d always confided in Dean, but he hasn’t been around for a while now.
“She ever finally tell you who your dad is?”
You laugh a little, shaking your head. “Uh, no, I guess not. A few months ago, she said she thinks he’s either from Puerto Rico or Guatemala. She’s not sure, but she remembers my father speaking Spanish.”
“Huh.” Dean’s brows raise slightly. “What happened to you being 13% Cherokee?”
“Yeah, more like a 100% lie,” you retort, chuckling. “Remember when she told me she thinks I’m half-Asian but couldn’t remember which part of Asia exactly?”
“Yeah.” Dean laughs softly, nodding. “You could do one of those DNA tests, though, right? I heard they’re a thing now.”
“I guess, but I don’t really care enough to do that, you know? I mean, I’ve lived thirty years without a father. Don’t see why I’d need one now,” you say, fingers playing with your taco shell. “Besides, judging by Connie’s type, I’m not sure I wanna know. What if he’s nuts like her, and I end up taking care of two crazy parents?”
“Guess that’s a possibility,” Dean replies, chuckling.
“And the rest is, you know, typical Connie shit,” you explain with a half-hearted shrug. “Remember when she told me to give you more blowjobs to avoid getting pregnant?”
Dean laughs loudly at the memory, wiping the tears brimming in his green eyes with his fingers. “Classic Connie... She also gave me a pack of condoms the first night I was staying over. We even got breakfast in bed in the morning.”
“Yeah, easy for you to say. Your childhood home doesn’t resemble Casa Erotica,” you remark wryly. “She keeps sending me these really weird articles about sexual liberation, too. Even got a book about Kama Sutra for Christmas.”
“Well, I don’t remember you needing help in that department,” Dean accidentally comments and instantly bites his tongue, his wide eyes finding yours.
You laugh lightly, your cheeks blushing. “Well, uh, thank you. Neither did I. And you don’t even know what new tricks I’ve learned over the last decade,” you quip flirtatiously, watching his jaw grind at your suggestion. You casually crumple your empty wrapping paper into a ball and look at him expectantly. “So, what’s next on our list?”
“Right, uhm…” Dean breaks from his stupor, clearing his throat. He wipes his hands with a napkin before rubbing them on his jeans. “Well, there’s really only one more spot I wanna take you to.”
“Alright, lead the way.” You smile, feeling the butterflies in your belly soaring high to the stars above.
▶️ Chapter 3: Old Sparks
The heat is turning up as the night progresses, and if you're thinking, "Hmm, Dean seems a little sus," you're probably right 😜
Get ready for more heat & angst next week!
Coming Up:
The nightly summer air is cool and crisp as the two of you settle into a comfortable and easy silence on the hood of the car, facing the horizon. For a heartbeat, you just breathe and enjoy the view, side by side. When you steal a glance at the backseat, Dean catches you and chuckles softly.
“What?” You arch an eyebrow.
“Nothing.” He laughs lightly, shaking his head. “I guess I just know where your mind went now. We’ve had some good times here, didn’t we?”
“Yeah, I guess so,” you agree quietly, but it’s not the reaction he’s hoped for.
“You guess so?” Dean cocks his brow at you and playfully nudges you with his shoulder, seeing the faint hints of tears brimming in the corners of your eyes. “Alright, what’s going on with you?”
“I told you. ‘M just tired,” you lie once more.
“Hmm,” Dean hums, not believing you even for a second. Ten years might have passed and both of you changed slightly, but he still knows you too well – better than anyone on this planet. What a fucking heartbreaking thing to realize. “C’mon, talk to me, sweetheart.”
“Not in the mood to talk, Dean. Just leave it be,” you reply and keep your focus on the twinkling town lights, trying to keep the tears at bay.
Have you ruined your life by leaving ten years ago?
“Alright, how about I start, huh?” You only offer him a careless shrug as a response, and Dean exhales a small sigh. He swallows thickly, his gaze fixed on his hands in his lap. “I lied to you earlier… in the diner,” he starts, and you meet his eyes with a tilt of your head then.
Okay little behind here so you may get spammed here 😂
Ok first I am not going to lie Bobby’s Junkyard does sound like a good diner name. Especially if the decor is like something you would find in a junkyard. But anyway Benny! I always love when he shows up you write him so well. But it seems Benny knows something with the way he keeps trying to get Dean to come talk to him. I don’t think it’s her cause Benny was sweet with her. So what is it maybe dean isn’t telling her everything. 🤔 Anyway this was so cute and fluffy they are having a great time. I think she is falling in love again but I know you Wayne some angst is coming soon! But I am going to enjoy this fluffiness while I have it. But I do have a feeling Dean did indeed read her books. Whew this is emotional already!
We are being fed with amazing Jensen content lately and I am loving it!! Jensen is looking so damn good. He just gets better with age I mean damn look at him! But seriously I am so proud of Jensen. Even though I am on episode 3 of Countdown hey I like to binge watch sometimes! Anyway I think it is a great show Jensen as Mark omg I love it! But I watch Jensen go from Eric Brady on a soap to 1 season roles to the amazing Dean Winchester who still has a place in my heart. He spent 15 years playing Dean Winchester so sometimes it’s hard to see him as other characters. But then we got Solider Boy, Russell and now Mark Meachum! Jensen is doing amazing he is on a hot streak! I do hope he does pace himself though I don’t want him doing too much to tire himself out. So proud of Jensen and I can’t wait to watch more of Countdown!
Jensen Ackles and Jessica Camacho Entertainment Weekly
Wow Entertainment Weekly really trying to kill me here! Cause DAMN Jensen is looking like a freaking snack here!! But in all seriousness I can’t express how proud I am of Jensen. I am so behind on Countdown I have only seen the first episode I haven’t had time to watch the rest. Hopefully I can soon! But I am still so proud of him. I seriously hope this show gets picked up for a season 2 cause this is an amazing cast!
Edit to add: From Soldier Boy to Russell to Mark Jensen is on a roll lately. Each character is unique in their own way. Btw I know there was Beau but I’m talking recent roles. But I love how he puts himself into each character. Dean Winchester will always have my heart but I can always make room for others. Besides I will always support Jensen in any of his roles. I can’t wait til we get to see Soldier Boy again!
Full Entertainment Weekly article: https://ew.com/countdown-cover-story-jensen-ackles-11771731
Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x Reader
Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, tiny bit of angst, fluff, 100% a romcom (Wayne's Version 😜)
Word Count: 3.9k
Posted on Patreon April 2, 2025
A/N: I'm so excited to do a Dean series again! I missed him 😩💚 This one's super fluffy with a lot of screaming in the middle. I took the premise from the movie of the same name, but it changes drastically after the beginning. Happy reading, friends!
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Chapter 1: Old Regrets
The blinking little line on an empty page screams at you. The more you stare at it, the more it morphs into a middle finger, giving the biggest ‘fuck you.’ How to start? What to write? What words to choose?
Shit, shit, shit…
Where is this character? What do you even want to write about? Do you even have a genre? A hint of an idea?
No, fuck, fuck, no…
You glare at the seven words on your screen, five of them curses – repetitive, too. God, you can’t even be creative with your maledictions. And is ‘no’ even a word that counts? It feels more like a cry for help.
You blow a raspberry and slump your shoulders with a sigh. Fuck, you’re screwed, aren’t you?
Your publisher will drop you if you can’t deliver a raging new bestseller in six months. Your first draft is due in four weeks – and that was after you’ve begged Rowena to extend your deadline. You’ll lose your job, you’ll lose your nice apartment in SoHo, and you’ll have to move back home to Kansas and live with your mom till you die there.
Great. Maybe you should write about that. You’re certainly feeling dramatic right now.
Softly, you bang your head against the keyboard, your word count exploding. With a frustrated groan, you rise and shut the laptop a little too harshly, sauntering into the kitchen to grab a bottle of wine and feed your cat, who announces his hunger with a loud meow as he hops onto the counter.
As you place the bowl in front of Hemingway and scratch his fluffy, orange head, your lips suddenly rise to a smile as a memory pops up.
“You know, sweetheart, if you ever get a cat, you should name him Hemingway.”
“Why? ‘Cause I love books?”
“Yeah! ‘Sides, I like Hemingway’s work. That cat should be happy to have a cool name like that.”
Wow. You haven’t thought about him in a long time. Your heart still does that little sting, albeit it’s been ten years since you’ve even seen him. Since you’ve talked to him.
Dean Winchester is one of the reasons you barely ever visit home. Maybe even the biggest one.
It’s hard not to think about him, considering the first three books, all bestsellers, were essentially all him. They stemmed from ideas that blossomed in the five years you’d spent together. But now you are all tapped out. You’ve said what you needed to get out, spun your fantasies in every which way, and rid yourself of the what-ifs.
But what if?
No, this is crazy. Thinking about your high school sweetheart you dated all through college? Maybe you don’t need the wine tonight, after all.
Your gaze falls to the big window and the sparkling city skyline that sprawls out behind it. You recognize the grandeur, the beating metropolitan pulse, and the colorful facets of the people that call it home.
And still, you feel nothing. There used to be excitement in your veins. You felt lucky to be here, to live your dream, to do everything you ever wanted.
And yet, you feel empty. There’s an ache in your heart that keeps telling you you’re missing something.
Aside from your failing career, you haven’t seen your mother in a while. Maybe it’s good to go back home for a visit, flee the noises of the city, and touch grass.
You need a fresh perspective. So after finishing three glasses of wine, you open your laptop back up and book a flight.
“Mom?”
Your voice echoes through your childhood home, swinging the front door shut with your foot as soon as you’ve shuffled your bags into the foyer.
“Honey, hi! Oh, I didn’t know you were coming,” she says with a bright smile, embracing you in a tight hug.
“What d’you mean? I called you and said I was coming,” you point out, chuckling uncomfortably. Your relationship with your mother is complicated. You love her, but she’s a ‘free spirit,’ which is code for your mother being a bit promiscuous.
The men she dates are never bad or have treated you with unkindness, but it was hard to go to school when your mother gave cunnilingus to half your teachers. Judging by the silky robe wrapped around her and her tits pressing against you, you assume she’s also having company today.
“Oh, I thought you were pranking me, honey.” She snorts a laugh and brushes a few strands of loose hair behind your ear.
“Y/N, hi! Good to see you, kid.”
You narrow your eyes at the half-naked man who appears behind your mother in the doorframe, only a flimsy bedsheet wrapped around his waist.
“Mr. Edlund?”
“Oh, honey, do you remember Chuck? He was your high school English teacher,” your mother reminds you as if your gasp and agape mouth didn’t already give that fact away.
“I know, Mom!”
“We’re very proud of you, kid,” Mr. Edlund says, smiling, and wraps an arm around your mother’s shoulders. He then slaps her ass, making her yelp and giggle. “You ready to get back in there, Connie?”
“Oh God…” You squeeze your eyes shut, shaking your head vigorously to get rid of the vivid image in your mind.
“Oh, honey, I didn’t raise you to be such a prude.” Your mother tuts and gently pats your cheeks. “Sex is a very natural thing.” She then begins to knead the knotted muscles in your shoulders. “Maybe that’s why you’re so stiff. Did you not read the article I sent you? When’s the last you had an orgasm, huh?”
“Oh my God, Mom!” Your cheeks are burning hot, your heart is hammering wildly, and no matter how sexually liberated someone claims to be, you can’t imagine they’d be normal about a conversation like this with a parent. “Okay, you know what? You guys just-… finish here–” Ew, ew, ew! “–and I’ll just-… Yeah, I’ll come back.”
You’re so fast out that front door again you can barely hear your mother’s “Thank you, honey!”
Strolling aimlessly around your old neighborhood, you walk till you reach the town center. On first glance, it seems like nothing much has changed in Lawrence. Sure, there’s new shops, a house façade here or there in a different paint color than it used to be, or fresh foliage and flowers blooming in the park, but the core of your hometown remains untouched.
It’s still the town you couldn’t wait to leave when you were younger. Only one person had almost made you stay a lifetime.
Your eyes then land on an all too familiar flickering neon sign – Rocky’s Bar & Grill. A smile creeps to your face as a string of memories floods your mind. God, you had more than one wild night in there – laughing with your friends, playing pool, drinking your own body weight, and even do some sexually liberated things in the public restroom your mother would certainly be proud of.
Curiosity and nostalgia drag your feet into the establishment, and you instantly feel the familiarity of this place rushing back to you. It seems like the bar has been frozen in time, not even the tacky decoration changed, which has already been outdated when you were a child.
“Y/N? Is that really you? Oh my God!”
Your head turns to the chipper voice behind the bar counter, your smile rising immediately as you recognize the redhead. Charlie hasn’t changed a bit, either.
“Yup, it’s me,” you say with an awkward little laugh and hug your friend.
Charlie and you used to be inseparable in school. Even after your move to New York, the two of you stayed in touch – until you got busier and busier and busier, eventually settling into your new life as you tried to forget about the old one.
“It’s really good to see you.” Charlie grins, and her welcoming warms your heart.
You swallow down the guilt bubbling in your throat. Are you actually an ass for ditching your friends? But that’s normal, right? People evolve and move on to different things. It’s just how life works. No need to feel guilty about anything.
“It’s good to see you, too.” You try to form a smile, but your heart only keeps beating faster. Maybe this is a bad idea. What are you even doing here? “I-, uh, thank you for all your newsletters, Charlie. Really. You know, I-, uh, I try to respond, but then my editor calls and, you know, book tours…”
God, you sound like an idiot.
“No, no, don’t worry about it. I get it. You’re a best-selling author. I’m sure you’re super busy. I can’t even imagine,” Charlie brushes your concerns away with her usual sunny smile, and you can tell she means it. It’s rare to find that in New York – people who still show honest kindness. “Just happy you’re reading them and haven’t forgotten about us.”
Well, you might have missed a few of them recently… You really are an ass, aren’t you?
“No, are you kidding? Of course I haven’t forgotten about you guys,” you lie with a forced laugh. Shit. “So, uh, how’s the gang?”
“Well, uh, as you know, Benny broke up with Andrea–“
“Uh-huh, yeah… How-, uh, how is he?” Needless to say, you had no clue they broke up.
“It was hard in the beginning, you know? I mean, after she cheated on him and everything…”
“Oh, yeah. So tough.” You nod your feigned agreement.
“Right? I mean, can you imagine? Anyways, he’s doing better now. He actually started seeing Donna,” Charlie tells you with a conspiratorial grin.
“No!” You gasp loudly, eyes wide. “Donna Hanscum? Sweet, little Donna is dating Benny Lafitte, high school quarterback?”
“Yup.”
“Hmm, you know what? They actually make a great couple,” you note musingly. You’ve never met two people with purer hearts.
“Right?! That’s what everyone’s been saying, too!” Charlie’s grin broadens, and you notice how easily you fall back into old habits once the initial awkwardness and shame subside. “Oh, uh, Cas and Meg are still going strong. Expecting their second kid.”
“Wow. That’s… surprising,” you joke, giggling.
“Yeah,” Charlie laughs her agreement, but then silence takes a hold. You know why. She doesn’t want to tell you about Dean, and you don’t exactly want to ask about him, either.
From Charlie’s newsletters, you always knew when Dean was out of town – every summer for the past ten years he had taken a road trip to California with his little brother. Considering it’s July, you feel relatively safe being here without the risk of running into your ex.
“So, uh, you work at Rocky’s now?” you ask to break the ice.
“No, uh, I’m still with Roman Tech,” Charlie says and holds up the tablet in her hand. “The bar’s just finally getting some Wi-Fi.”
“Oh, yeah, of course! About time Lawrence made it to the 21st century, right?”
“Yeah, I mean, that’s what I’ve been saying since school. The only internet we used to have was in the public library. Remember that virus we accidentally downloaded when we tried to get that pirated version of the new N*SYNC album?”
“God, yeah, we crashed the whole system. Mr. Metarson was so mad,” you recall, laughing. “Well, uh, I should probably let you get back to work.”
Charlie nods, smiling. “It was good to see you, Y/N. You should come home more often.”
With a deep sigh, you then order a whiskey from the bar and settle down in a quiet corner booth at the far end. God knows you don’t want to run into more blasts from the past. You should’ve never come here. What did you think it would accomplish?
You surely haven’t come up with an idea for a new book so far and have only been reminded of old regrets instead. This hasn’t been your home for the last ten years. You have no place here anymore.
Finishing your drink, you jot down ideas on a small napkin – all of them terrible. You huff a sigh and crumple the useless notes. Curling your lips, you pick up your empty tumbler. Maybe another one is fine? You’re sure it’s past noon somewhere, just as you’re sure your mom and her new lover are nowhere near done yet.
You glance up when the door of the bar swings open, hearing the first few notes of his voice. It’s deeper than you remember, but you recognize it all the same.
Fuck. He’s not supposed to be in town! What the fuck is he doing here?
Your eyes widen and take everything in before you. Ten years have done nothing to Dean Winchester. In fact, he looks even more handsome than the last time you’ve seen him. His jaw is more defined, there’s scruff on his cheeks and throat that make him look more rugged, and there are soft, kind crinkles around his green eyes.
Why does your ex have to look so downright fuckable?
Shit! You’ve just gotten off a plane this morning! You didn’t exactly have time to check a mirror when you fled your mother’s house.
What should you do?
As Dean greets Pamela at the counter, you decide to slide under the table and hide there. This is a nightmare. You cannot face your unfairly hot ex-boyfriend like this.
“Y/N?”
Fuck! Why the hell is he coming over to you? Doesn’t he know about the unspoken rule to avoid your ex at all costs when you see them in public?
“Dean! Oh my God, hey!” You shuffle back onto the bench with as much nonchalance as you can find.
“Were you just hiding under the table?”
“What? No, don’t be ridiculous.” You snort awkwardly, your cheeks heating in fluster. Your hand desperately forages for something on the sticky floor till it grabs the first thing it can find. “I was just looking for my–,” you glimpse at the semi-hard and semi-wet item between your fingers, “–gum.”
Ew, ew, ew, ew, ew! You’re holding someone’s used gum. God knows what diseases you’ll contract after this, feeling the germs already soak into your skin.
Dean cocks an eyebrow. “Were you gonna put it back into your mouth or–“
“No, no…“ You shake your head, swallowing thickly. Your hand fumbles for the crumpled napkin before you discard the gross gum in there. “I was just picking it up. I didn’t wanna leave it there, you know? I heard it’s, uhm, bad for the, uh, bar floor environment.”
God, he probably thinks you’re an idiot.
“Right, yeah.” Dean chuckles politely at your bad attempt at a joke, scratching the nape of his neck.
Is he nervous? You remember he used to do that whenever he was anxious. He also still seems to have a preference for wearing flannels, the material perfectly hugging his broad shoulders and barely hiding the muscles on his arms.
“So, uh, what are you doing here?” you ask with the friendliest smile, trying to push all the uncomfortableness and embarrassment down.
“I was just about to ask you the same thing,” Dean replies and crosses his oh-so muscular arms over his aforementioned broad chest, the corners of his lips quirking with a curious smile. Is he flexing? “You barely ever come home. I mean, I don’t think I’ve seen you since… welp, the break-up, I guess. What’s it been? Ten years?”
“Really? Ten? Wow, crazy,” you say and ignore your thundering heart as best as possible. You either are close to throwing up or passing out. “Well, you know, I’m just here visiting my mom. I’m currently writing my fourth book. Just figured it’d be nice to get out of the city for a few days, clear my head…”
“Right, yeah, uhm, congratulations! New York Times bestselling author, huh? You really made it,” Dean says and smiles, but you can tell it’s forced, and you think you know why. “Proud of you,” he still adds.
“Yeah, uh, thanks.” You clear your throat and shake your head a little. Why is there such a weird feeling in your stomach? “But, uh, what about you? What have you been up to? Did you become a firefighter like you wanted to?”
“Uh, no, actually,” he replies, pursing his damn plush, kissable lips. “I-, uh, I stayed on with my dad. Family business. He’s not getting younger, you know? Kinda needs my help.”
“Yeah, no, totally get it. As long as you’re happy, it’s good, right?” Your heart hurts a little at the thought of Dean giving up his dreams to please his father. But you’re sadly not that surprised, either. He’s always been one of the most righteous, loyal, and dutiful people you know.
“Yeah, uh, I’m-… I’m happy. Business is going good, you know? And the old man actually lets me make decisions now,” Dean shares, chuckling.
“Wow, John Winchester letting go of control, huh? Thought I’d never see that,” you joke, earning you a warm laugh.
“Trust me, me neither, sweetheart,” Dean says with a chuckle but then notices how your brow raises at the old nickname. He scratches the back of his neck again, subtly clearing his throat. “I-, uh, I’m sorry. Old habits die hard, I guess.”
“Oh, uh, no worries. It’s fine,” you brush it off but can’t deny the way your heart is fluttering with butterflies you thought had perished ten years ago. He still seems like the same sweet guy, and you could just fall right back in love with him.
But that’s crazy, right? You can’t just start something up with an ex from ten years ago, can you? Besides, like the rest of your friends here, Dean’s probably already mated for life and has procreated by the multiple, succumbing to the charmed small-town destiny. Still, you can’t help your gaze from drifting to his massive hands and thick, long fingers, noticing there’s no ring there.
“Well, uh, anyways, we just opened our fifth location down in Wichita,” Dean tells you proudly.
“Wow, that’s great, Dean. I’m glad you’re doing well.” You send him a warm smile, nodding, and then recognize the strange silence sneaking back in. “Well, uh, it was good to see you. Take care, okay?”
“Yeah, yeah, you too.” Dean turns halfway, licking his lips. He hasn’t even managed a full step yet before spinning back on his heel to you. “Hey, uh, I was gonna grab take-out, but do you want some company? C’mon, I’ll buy you a drink. You drink beer too or just whiskey before noon?”
You snort a laugh at the teasing grin on his face. How can he be so charming and easy to talk to? Just like in high school, you fall victim once again to Dean Winchester’s irresistibility.
“No, uh, I’ll take a beer, too,” you agree with a wide smile.
“Took two years to build, but I’m really happy how it turned out,” Dean tells you as he swipes through pictures on his phone, showing you his life.
“Wow, building your dream home on the plot next to your parents. You really double-downed on staying in Lawrence, huh?” you tease, although there’s pain in your heart you try to conceal.
Dean chuckles, nodding. “Yeah, well, someone has to take over, right? Sam decided to stay in California when he married Jess, so…”
“Wait, little Sammy got married?” You gape at Dean, involuntarily leaning closer. You playfully touch his forearm that rests on the counter, but he doesn’t seem to mind as he coolly nurses his beer.
Is history repeating itself? Maybe this time, you could change the outcome, though.
“Yeah, uh, they’re actually expecting their first kid this fall,” Dean shares, and you can see the pride in his mesmerizingly green eyes. You’ve almost forgotten their vibrancy over the years. They’ve always been one of your favorite features about him.
“No way! Wow, we’re getting old,” you say, giggling. You still remember meeting Jess when you and Dean drove down to California and visited Sam during his freshman year at Stanford. It had been one of your last road trips together before the two of you broke up.
“Yeah, I know.” Dean laughs and takes another gulp of beer. “So, when was the last time you actually came home, huh?”
“Hey, I come home almost every summer. And Christmas. Sometimes…” You begin to rethink under his scrutinizing look. “Well, maybe not the last few years. Guess it’s been a while.” You give a shrug of your shoulders, but Dean’s brow only raises higher. “What? New York is pretty irresistible around Christmas, okay?”
Dean chuckles triumphantly, shaking his head. “But you don’t have to live there, right? You could write anywhere,” he points out, and you know that particular topic is a sore point for him.
“Yeah, I guess now I could,” you admit and meet his forest-green eyes, seeing a million questions in them he doesn’t dare to ask. “But there’s nothing here for me anymore, you know? I mean, my mom, sure. But she visits me three times in New York every year. I don’t really have a reason to come back here.”
“Wow, really hard to see you from that high horse,” Dean wisecracks, chuckling.
“Wha-, c’mon!” You scoff a laugh. “You know I didn’t mean it like that. Lawrence is great. I just have more opportunities in New York.”
Dean suddenly rises from the barstool, finishes his drink, and holds out a hand to you, nodding toward the door. “Alright, c’mon.”
“Where are we going?” you ask but still take his warm hand, your own feeling small in his, as he leads you back into the bright daylight.
And there, you see it – the classic, sleek black beauty he calls his Baby, parked meticulously by the curb of the sidewalk, untouched paint coat shining in the sun.
“Can’t believe you still got the Impala,” you breathe, an entranced gleam in your eyes.
Dean lifts a brow. “‘Scuse me? The day she leaves my side is the day I die.”
You press your lips into a tight line, but the teasing grin slips through. You still remember where to poke the bear. Turns out it’s like riding a bike – you never truly forget.
“Wow, so I guess the obsession with the car hasn’t changed, either.”
“What d’you mean?” Dean furrows his brow, close to offended, and you stifle the bubble of laughter that wants to erupt. “Look, aside from you, she’s my first love, okay?”
Bobbing your head, your brows hitch before you smirk at him.
Dean huffs a sigh, rolling his eyes. He rounds the front of the car to the driver’s side, opening the door. “Alright, get in and shut up.”
Giggling, you accept his invitation, your fingertips feeling the familiar, worn leather of the seat as a flood of memories crashes right back at you. God, you can’t even remember how many hours you’ve spent in this car with him, but they did feel like they were endless.
Until they ended.
“Can I pick the music?” you ask with a teasing grin, although you know the answer too damn well.
“Rules haven’t changed, either. Driver picks the music, shotgun shuts their cakehole,” Dean says, chuckling, and starts the engine.
“So, where are we going?”
Dean smirks. “Down memory fucking lane, sweetheart.”
▶️ Chapter 2: Old Haunts – JUNE 18
This series might start cute and fluffy, but don't let that fool you. I promise you you'll curse me soon enough 😂 Reader's mom also might be one of my favorite parents ever. She was based halfway on the mother in the movie and the mother from Friends With Benefits. Love me a good hippie mom 😜
Coming Up:
“Okay, stay here. Don’t you dare move.” Dean grins victoriously and rushes past you to the far end of the diner, and it suddenly dawns on you what his plan is.
On cue, the diner fills with music from Bobby’s old jukebox, playing a song Dean just picked. You recognize it immediately and send him a raised look, partially amused by his choice as Can’t Fight this Feeling starts.
“Really? REO?”
“C’mon, it’s our song,” Dean argues goofily and joins you again in a few strides.
“Yeah, and like I told you back then a million times, I refuse to accept that,” you retort, laughing.
“Welp, don’t care,” Dean quips. He then holds out his palm, smirking. “Will you do me the honor and accept this dance, Ms. Y/L/N?”
You chortle but hesitantly agree to his offer, placing your hand in his before he pulls you flush against his body in one suave motion. His other hand comes to rest on your lower back while yours lands on his shoulder, feeling the dips of his muscles under your pads.
“It’s the song that played the first time I asked you to dance during our junior prom. Remember that?” Dean’s eyes find yours as you get lost in his embrace.
Goddammit, you’ve missed those arms around you. They make you feel safe and loved. They always have, and now you’re sure they always will.
Yay glad this is out here cause I need some mechanic Dean in my life. There is just something about Dean being a mechanic that drives me feral I don’t know why! But I love it! 😂 So let’s dive in here!!
feed your cat, who announces his hunger with a loud meow as he hops onto the counter.As you place the bowl in front of Hemingway and scratch his fluffy, orange head
first off omg I can relate to this cause I actually have a orange cat who will meow so loud when he is hungry. Soon as he sees me in the kitchen during his feeding times and meows loud til I feed him. Only thing is his name is Scooter not Hemingway he is named after a muppet. 😂 I also have a white cat named Casper he just stares at me. But I loved this part cause it made me think of my 2 boys.
my orange boy btw
Yeah he sleeps like he is dead after he is satisfied with his meal. 😂
Moving on cause I can talk about my two boys all day. Anyway the part with her mom omg! That cracked me up I couldn’t stop laughing. I also got a little traumatized remembering being a little kid and walking in on my parents. 😳 But I will not think of that here no no! But I love her mom can’t wait for more of her!
Charlie telling her everything that happened I was like girl you should have went home more how dare you!! Hopefully she finds a reason to stay home.
Her reunion with Dean was so cute it was sweet. But I know you Wayne you will break my heart a little before healing it again. So I am going to hang onto this fluffy part for as long as I can! But I can’t wait to see more of their story. Maybe some sexy time too cause I’m a ho for dean smut! 😂 great first chapter Wayne I can’t wait for more!!
Jensen blessing us with a IG post and he is looking so good!! I am so proud of Jensen and I can’t wait for Countdown!! For now I am going to enjoy how good he is looking right now!!😍❤️
Also next Monday June 23rd Jensen will be on The Tonight Show staring Jimmy Fallon. It airs at 11:35pm eastern. Oh & yes I will get back to posting more here!
Series Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x F!Reader
Warnings: 18+ for language & things I won't spoil yet, past Dean x reader, small town AU, a self-finding journey, nostalgia, exes to lovers, slow burn, idiocy may heavily occur, tons of humor, angst, hurt, fluff, 100% a romcom (Wayne's Version 🛠️)
A/N: *classic 2000s trailer voice* Inspired by the movie of the same name, here comes another romcom that will make you laugh, cry, scream in frustration, and fall in love all over again 😉🧡
WAYNE!! I need to catch up on some things of yours and start your latest Soldier Boy/Ben series. But I can’t wait for this!! Mechanic Dean is my weakness!!! I need more of him in my life like now! If I wasn’t a broke girly I would get your patreon so I can read this now! Cause I’m an impatient girly at times 😂. But I can’t swing it right now hopefully soon I can though. But I can’t wait for this!!!
Christen!!!! Omfg it’s been forever?!?! Hope you’re well, friend! I missed your screams 🥰🫶
And yup, mechanic!Dean surely is something. Every time he’s under a car, I wanna be under him… 🫠
PS: No worries about Patreon, love! There’s no pressure at all. I got it to combat mom guilt a little and made it a savings account for my little one, so I can pursue my hobby in peace without the constant “I should slave away for him only and forget who I am as a person” 😂🩵
It has been forever! I spent all of 2024 in a very rough patch both mentally and financially. So I was barely here much. But luckily in January 2025 things financially started to get better. Mentally I am working on it but I am happy to be posting again! I can’t wait to read things I need to catch up on & your current Soldier Boy story. But first I see Chapter 1 is out so I gotta go read it! Prepare for my happy screams and what are you thinking screams more often!!
ah yes the littles I always say they are adults trapped in kids bodies. My baby cousins are the same. Luckily the only littles I have for now are fur babies. Although they are expensive too only difference is they can’t talk except to bark(my diva dog) or meow(my 2 boys) but I am sure they mean that too. 😂 ❤️
Series Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.
Pairing: Mechanic!Dean Winchester x F!Reader
Warnings: 18+ for language & things I won't spoil yet, past Dean x reader, small town AU, a self-finding journey, nostalgia, exes to lovers, slow burn, idiocy may heavily occur, tons of humor, angst, hurt, fluff, 100% a romcom (Wayne's Version 🛠️)
A/N: *classic 2000s trailer voice* Inspired by the movie of the same name, here comes another romcom that will make you laugh, cry, scream in frustration, and fall in love all over again 😉🧡
WAYNE!! I need to catch up on some things of yours and start your latest Soldier Boy/Ben series. But I can’t wait for this!! Mechanic Dean is my weakness!!! I need more of him in my life like now! If I wasn’t a broke girly I would get your patreon so I can read this now! Cause I’m an impatient girly at times 😂. But I can’t swing it right now hopefully soon I can though. But I can’t wait for this!!!
