Somebody I Used to Know – Chapter 8
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, humor, 100% a romcom (Wayne's Version 😜), a tiny bit of angst, some revelations, tons of the fluffiest goddamn FLUFF
Word Count: 9.8k
Posted on Patreon June 5, 2025
A/N: The end of the road – literally! I honestly think this is the fluffiest ending I've ever written. Went full romcom and not regretting a single word of it lol. This entire part was so fun to plan. Hopefully, this makes up for all the angst I've put you through. Now, get ready to be swept off your feet by Dean Winchester 😉💕
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Chapter 8: Old Ties
You’re not ready for this day to be anything.
You’ve spent the last forty-eight hours holed up in your childhood bedroom, surrounded by unpacked boxes, a stack of notebooks that are half filled by now, and an ever-growing and weird to-do list from your mother.
You told yourself you were here for a reset. For space. For clarity. But the truth is, you don’t know what the hell you’re doing anymore. You’re more lost than ever.
You think about leaving – more than once.
Actually, you nearly do three separate times before lunch. Once with your bag half-packed on your bed, once when your mother asks if you can pick up her dried lavender from the farmer’s market, and once again standing in line at the coffee shop behind Jo of all people.
She told you she was leaving town and going on tour with her band. She seemed happy. Glowing. Free.
Which seems almost crazy, considering she just broke up with a guy she wanted to marry tomorrow. And again, you wish you could be her. You envy that happiness. That freedom. That peace.
Instead, you’re still sulking over the same damn boy since you were a teenager.
You can admit as much, though not out loud. To yourself, maybe. To the empty cereal bowl sitting on the coffee table. To the ceramic rooster lamp your mother bought on clearance and insists brings “gentle morning energy” to the kitchen.
Alright, fine. Maybe you’ve reached the point of sulking where even your chipped coffee mug seems to judge you.
It’s been two days since Dean Winchester threw a literal wrench into your carefully fortified emotional barricade by looking at you like you were still his favorite story.
Two days since the roadside ambush he orchestrated with the help of your mother. (Okay, “ambush” might be a strong word. You did need the car fixed. But still.)
Two days since he showed up with a cocky smile and toolbox in hand, pouring his entire damn heart out under the hood of a sputtering Honda like the two of you were characters in some goddamn low-budget indie movie about fucking regret and second chances.
Two days since you said you wouldn’t get back together with Dean Winchester.
And two days since you’ve started thinking about it anyway.
You told yourself you were done. You even said it out loud in the mirror. But the trouble with heartbreak – especially when it comes in the form of a man who knows your coffee order, your tells in poker, and the songs you can’t sing without crying – is that it’s never really clean.
Not with Dean. Not with your hometown. Not with all the pieces of yourself still lodged in this place like shrapnel.
You still remember the look on his face as you drove away – hopeful, determined, maybe a little destroyed. You’ve been trying to pretend that memory didn’t brand itself into your ribcage like a signature.
But it’s there.
Worse – it’s joined by others. The way he fixed the car without looking at a manual. The way his voice cracked when he said he never stopped loving you. The way you almost cried right in front of him.
You didn’t – but almost.
And sure, maybe you wavered just a little when he talked. Maybe the familiar way he said your name loosened something deep in your chest.
Maybe.
You’ve been trying to write – you really have. Get all your emotions out. Sticky. Messy. Honest.
But right now, you’ve been sitting on the floor of your childhood bedroom for hours, notebook open, fingers limp around your pen, and every word you manage to scrape out reads like it was written by someone else.
Someone flat. Hollowed out. Cool. Over it. Unbothered.
And you’re fucking bothered. That’s the problem.
You still feel his voice, that bourbon-warm rhythm of his words, tucked under your skin. It feels like those words belong to you now, stitched right into your bones.
Still, you can’t seem to bring them onto paper.
Because now? Now, you’re not mad anymore – not exactly. Not like you were. Now it’s something worse.
You fucking miss him.
You hate how true that feels. You hate even more how much you want him to prove he’s not full of shit. That he meant what he said in that sunlit street with your hood popped and heart split wide open.
That you still mean something to him.
But you’re an author. You know better than anyone that words can be dangerous, especially ones that come too easily.
And Dean hasn’t tried again. Not since then. No unexpected knocks. No more last-minute breakdowns. No notes taped to your window. The silence is probably supposed to be respectful.
But it fucking gnaws on you.
You close the notebook with a frustrated thud and lean back against your bed frame. You’re still in your pajamas – if an old band tee and underwear even count as such.
God, you’re pathetic. This is a low point in your life.
And that’s when your mother floats into the room like it’s the Summer of Love, holding something behind her back. Her hair is braided with small beads. She’s wearing a sundress with more holes than fabric, a poncho made of recycled hemp, and the kind of smile that means she’s absolutely up to something.
You want to groan upon entry. Not again…
Moreover, she’s got that look on her face – the one she wore when you got your first period, or when she walked in on you and Dean in a compromising position on the basement couch. You can still see Dean’s proud fucking grin in your mind when she complimented his form.
You wish those would be the only embarrassing stories, but there’s a lot more where those came from.
“Hi, sweet pea,” she sing-songs brightly. “Oh good, you’re not wearing pants. You’ll want to be comfortable.”
Your eyes narrow. You’ve lived with this woman for way too long to not be suspicious. “What are you up to?”
“Nothing.” She shrugs way too innocently for your taste. “I just have a special delivery from the universe.”
You roll your eyes and sigh in a way that makes you feel like a teenager again. “Mom, I already told you a peyote trip is not gonna help.”
“Disagree. You’d be surprised,” she says all too casually and then grins. “But what I have for you is much juicier than that.”
She reveals the object behind her like a magic trick – a small envelope with your name scrawled across the front.
Bold. Messy. All-caps. It’s his.
Your mother plops down next to you on the floor like she’s still twenty and made of air and hands it to you with that same little grin that doesn’t seem to go away.
“I think you’ll want to open this,” she says gently and pats your thigh. “It’s from a man with sad green eyes who clearly worships the ground your gorgeous ass walks on.”
“Mom–”
“He said, ‘Don’t tell her it’s from me, or she’ll burn it,’” she says with a wink. “So naturally, I told you.”
You sigh once more in defeat and then glance at the envelope in your hands for a few seconds longer before tearing it open, your heart doing that stupid thing where it jumps like it’s seventeen and hormonal again.
Hey, I’ve never been good with words. Not like you. You were the one who always found the right ones. I never knew how to string them together the way you do. But I’m trying. If you’re reading this, it means you haven’t set it on fire – yet. Good start. That’s already more than I deserve. I figured the only way to explain everything was to remind you of what I never forgot, so I’m going to let the places we made memories do some of the talking for me. Hope you’re still good at riddles. Start where your stories live. The place you used to go when the world got a little too loud. Quiet corners, creaky shelves. The redhead who always knows way too much about us is waiting for you there. I’ll meet you at the end after the last clue. Unless you still hate me, then I’ll go quietly. Promise. –D
You stare at the letter for a long beat. “He’s kidding.”
“Isn’t it romantic?” your mother swoons. “He’s doing the grand gesture thing, honey. I haven’t seen something this tender since your father played Crimson and Clover on a didgeridoo outside my yoga tent.”
You snort and arch an eyebrow. “And what father would that be this time?”
“The real one,” she says with a wink and squeezes your cheek.
With a sigh, you fold the note, heart hammering louder behind your ribs than it should.
The bookstore. Charlie.
You don’t mean to follow a breadcrumb trail set by the guy who wrecked your heart and still somehow owns every piece of it. You really don’t. You tell yourself you’re just curious. That’s all.
But before your head can protest too much, you slip into a sundress, grab the keys to your mom’s old car, and head out the door. Hopefully, there aren’t any more stuffed animals under the hood this time.
You park outside the bookstore ten minutes later. You push open the weathered door, the bell jingling overhead. It smells the same – ink and cedar and that faint lingering scent of peppermint the owner swears she doesn’t use. You haven’t stepped foot in here since you came back to town. You thought it’d be too hard, too... evocative.
This place still wraps around you like a well-worn cardigan. You used to hole up here for hours in high school, losing yourself curled in the corner window seat with headphones on and three different books in your lap, trying to block out the ache of being a teenager and in love for the first time.
But Dean always found you here. Brought you a cup of coffee and sat beside you with an arm slung across the back of the couch, pretending he didn’t like books. Too cool. He always fell asleep halfway through motorcycle magazines.
Charlie is perched on a stool near the register, wearing a shirt that says Plot Twist. Of course she does. “Took you long enough,” she says, grinning like a co-conspirator.
You narrow your eyes. “So you’re in on this.”
“Dean came by the house,” she offers as an explanation for her betrayal. “Said he needed help not screwing it up. I mean, obviously I said no at first. But then he practically begged. Said he needed someone smart and snarky and emotionally available. He also bribed me with coffee and Oreos. I’m weak, okay?”
You giggle a little, not being able to help the smile that wants to spread. “What now?”
“Oh! He said you’re supposed to find his favorite Hemingway book. Said you knew which one,” Charlie says.
You groan loudly, throwing your head back. “Of course he picks the most depressing-ass book…”
It doesn’t take long. Second floor, third aisle, left-hand side. Your fingers hover over the row, then land on A Farewell to Arms.
He used to call it his “angry rainy day book.” You always hated the ending. Said it was bleak and cruel. Dean argued it was honest. Life was cruel. Love didn’t always win. But he always shut up fast when you glared at him.
Inside the back cover is another note, folded around a pressed wildflower. You recognize the flower. He once plucked it from the side of the road and put it in your hair after a high school bonfire. You never knew he even kept it.
You cried at the ending and threw it across your bedroom. Told me it was too honest. You said that’s what hurt the most. You always hated stories that ended without fixing what broke. I used to sit on that couch and pretend I wasn’t watching you read. I loved the way you curled up like you belonged there. You were always home to me. Next stop? Go to the place where I first told you you were pretty. Hint: you threw a fry at me right after. Ask the man who makes the worst pancakes but has the best advice for your next clue.
Charlie claps wildly. “You win a prize! It’s a Benny!”
You're still reluctant, but somehow your feet drag you further down the road anyway.
Bobby’s Junkyard Diner isn’t busy this time of day, but Benny’s already placing a basket of fries and a strawberry milkshake down on the counter like he’s been expecting you as you take a seat in front of him.
Ten years ago when you sat in your usual booth, you and Dean were fighting about your future – his fear, your ambition, your shared inability to speak the same language when it mattered.
“You’re a good woman,” Benny says, grinning with a dish rag over his shoulder like some Southern version of a sitcom dad. “You didn’t have to come.”
You snort and snatch a fry. “Let me guess. You’ve got a note under a plate of pie or something?”
He chuckles. “Close.”
He reaches behind the counter and pulls out a napkin. Folded neatly, with Dean’s unmistakable scrawl.
You always said this place was the only one that knew how you liked your bacon. I liked watching you here – half-asleep, coffee in one hand, book in the other, scribbling stories onto napkins. This was where I knew. Right here. You were in that godawful Aerosmith band tee, arguing with Cas about The Empire Strikes Back, and I thought: that’s it. That’s the girl. Head to where I’d go when I needed noise to match the static in my brain.
“Man’s been sweating over these notes like they were a parole hearing,” Benny mutters. “You know where to go?”
You nod and smile. “Record store.”
The record store hasn’t changed much. Same crooked shelves, same tinny music overhead, same cat sleeping on the listening station like she pays rent. Dean’s vinyl guy still smells like cloves, and the floor creaks under your sneakers. Dean used to test you here – quizzing you on artists, albums, and liner notes.
You find Cas in the corner, holding a record sleeve like it might bite him.
“I’m surprised you’re here,” you greet him with a smile.
“Against my better judgment,” Cas mutters with a sigh.
“You don’t really listen to this stuff, do you?” you ask, nodding toward his hands.
“I do now. Dean made me a mixtape for my thirtieth birthday,” he says. “He wanted me to tell you to look for his favorite record.”
You give him a nod, your fingers already flipping through the ‘L’ bands of the classic rock section. “It’s Zeppelin II. He always tried putting it on during… well, you know.”
“I do know,” Cas replies, his blue eyes begging you not to continue.
You find the note tucked inside the gatefold of the album, along with a Polaroid – one from back in college, where you’re sitting in Dean’s lap at a house party, holding a beer and smiling like you hadn’t learned the word regret yet.
This is where you told me that Physical Graffiti sounds like teenage sex and motorcycles. You weren’t wrong. I know I screwed it up with our song, and I’m sorry. But I always imagined our first dance at our wedding would be to “Thank You.” It’s the one that ran during the first time we–… Well, I don’t know how graphic I’m allowed to make these notes (or how much of them our friends will read). But it’s ours now. Yours. Because at the end, there will still be you and me, sweetheart. Your next stop is where you used to steal my leather jacket and hide out during lunch. Sam says it still smells like weed.
You bite your lip and feel the lump forming in your throat. The high school.
The building looms the same way it always has – equal parts memory and menace. You used to sit on the bleachers with Dean, hands intertwined beneath the stars, passing notes like you weren’t already writing entire novels inside each other.
Sam’s waiting at the front steps of the school and smiles when he sees you – that soft, little-brother expression he saves only for you and Dean. Somehow that feels right. Jess is standing next to him and waving like you’re arriving for a picnic.
“Thought I might find you two here,” you say, smiling.
Jess bounces on the balls of her feet like she’s trying not to blurt the ending, all sunshine and knowing smiles. “You’re doing great! Like, so great. This is basically a Nora Ephron movie now.”
“Didn’t have Dean sending you on a romantic scavenger hunt on my apocalypse bingo card,” Sam wisecracks, amused. “I almost texted you to skip this one, but he’d kill me.”
Jess elbows him. “C’mon, it’s sweet!”
Sam sighs. “I’m not saying it’s not. Just… elaborate. Guy used to think flowers from a gas station counted as romance.”
You snort a laugh. He definitely did.
“You should’ve seen how nervous he was writing this one,” Jess says, handing you the envelope.
“Kept scratching stuff out,” Sam adds.
The next note is sealed in an old concert ticket from your first show together – Metallica, 1997. The two of you drove over 300 miles to Oklahoma City for it.
Remember when you wrote me a poem and passed it to me during Calculus? Mrs. Moseley caught us and made me read it out loud in front of the entire class. It said that I kissed like a sinner and prayed like a saint. We got detention for a week. Worth it. But I never told you it’s because you made me believe in things I never had before. I loved you before I even knew how to say it. You were always smarter than me. Braver too. I didn’t get a lot of things right back then. But I got this – us. And I’d fight for that every time, even if I fumble the landing. Now go to the place where I finally figured out how to fix things. Where I’m still trying. Tell Garth I said not to touch the stereo.
“You hanging in there?” Sam asks gently, probably noticing the tears brimming in your eyes.
You nod, but this scavenger hunt down memory lane feels like it’s trying to kill your heart slowly.
“For what it’s worth, we’re rooting for you. Both of you,” Jess says and winks.
The garage still smells like grease, motor oil, and gasoline. You walk in to find Garth tinkering under a hood, music blaring from the speaker behind him that sounds suspiciously like Taylor Swift.
He pops up when he sees you. “Ah! The chosen one.”
“Let me guess – Dean left you a note?”
“Ding ding ding,” Garth says, handing you a wrench with a wide grin. The note is taped to the handle.
You hated the noise in here. Said it messed with your focus. But you came anyway and brought your notebook, curled up on the old couch in the back, and wrote next to me while I cursed at carburetors. You made it feel like home. The next stop’s where we carved our names into the bark that summer before college. You took my pocketknife and misspelled your own name. Now you might find something new etched beside it.
You laugh a little. Dean’s never let you live it down that you wrote your own name wrong.
You say goodbye to Garth and Kevin and make your way to the park and the old oak tree. It’s sunset by the time you get there. Dean took you for a picnic here the night before college started. You carved your initials and his. Even though it felt cheesy. Even though you both pretended not to care.
You trace the carving with your fingertips. The original still stands – crooked and weathered, but untouched. Your name’s still wrong. But right below it, there’s a new one:
Forever.
You crouch beside the roots and find the note tucked between two stones. No envelope this time. Just ink and hope.
Knowing you changed everything. Knowing myself took longer. You always thought you had to be everything for everyone. That you had to earn your place, your worth, your story. But you already were everything to me. I couldn’t tell you what you deserved back then, because I didn’t know what I deserved either. But I know now. You always said you felt like half a story, so I think it’s time you get the full one. You deserve to know yourself, not just who you were in my story – but in your own. I’ll be waiting just a little ways behind you.
You lower the note slowly, heart pulling at every tether inside you. You know instantly what he means. How the hell did he–
But before you can ask yourself too many questions, you feel it. The shift in the wind. The scuff of boots on grass.
You spin around, and Dean’s there, hands in his jeans pockets, eyes wide and nervous. No grin. No smirk. No swagger. Just standing there like a man who knows what he wants and is terrified he might not deserve it – hopeful and more real than memory ever lets him be.
“Hey,” you breathe, barely getting the word out.
“Hey, you made it,” he says softly, stepping closer. “Look, I know it’s not enough, and I know this doesn’t fix what I broke. But I needed you to know I’ve been paying attention. Even when you thought I wasn’t.”
You hold up the note then. “What, uh–”
You honestly don’t know what to say. You’re out of words for once. Completely and utterly speechless.
“Yeah, about that…” Dean starts and scratches his throat. “Look, if you’re not ready, we can skip this one and go straight to the last one, okay? You don’t have to do anything today. But if you do want to know, he’s just a few miles away.”
Your jaw drops slightly, brow hitching high. “He lives in town?”
Dean nods slowly. “Yeah, I spoke to your mom last night.”
“She tell you how to make moon water with a quartz crystal and the tears of a Capricorn?” you quip and cross your arms. Humor has always been your armor.
Dean snorts, the corners of his mouth lifting. “Nah, but she told me the truth. About your dad.”
“You sure she told you the right one this time?”
“Yeah,” Dean says, nodding. “Pretty sure. Got her to finally say it. She said she wasn’t trying to hurt you – just thought it’d be simpler that way. For everyone. But I told her you deserved better than that. I talked to him, too. He’s already expecting you. No pressure, of course.”
“He actually wants to see me?” you ask cautiously. You’re not eager to blow up some poor guy’s life tonight, who once fell into bed with your mother three decades ago.
“I think he’s been waiting a long time,” Dean replies. “I’ll be with you every step of the way, alright? Or if you’re still too mad at me, I can call Charlie, your mom–”
You interrupt Dean with a shake of your head, swallowing. “No, I want you.”
Your answer seems to surprise both of you.
“You’re gonna tell me who?” you ask then.
Dean exhales, like he’s been waiting for you to ask. “I think you’ve always known.”
“Maybe,” you admit quietly. “Maybe I always had a feeling. But there’s a difference between knowing something in your bones and hearing someone say it out loud.”
“I know.” Dean nods and holds out his hand for you to take. And you do, interlacing your fingers with his. He gives it a gentle squeeze. “Ready?”
“Guess so.”
This next stop isn’t just another piece of some sentimental puzzle. It’s the truth you’ve been denied for three decades. You think about all the years of questions. The blanks. The lies. All the times you’d watch other girls dance with their dads at weddings and tell yourself it didn’t matter. You had your mom. You had grit.
But maybe now you could have something more.
You don’t even realize how tightly you’ve been gripping Dean’s hand until he gives yours a little squeeze.
“Relax,” he says as he pulls the Impala into the long gravel drive you know by heart. “You’ve been here a hundred times.”
“Well, not like this,” you mutter.
The little ranch-style house looks the same as always – weathered siding, mismatched porch chairs. The screen door squeaks. There’s a dog bowl by the steps, a cracked birdbath in the front yard, and an old Chevy truck in the drive.
You step out of the car together, and Dean strolls with you up a path between towering pines, your shoes crunching on the gravel. The door creaks open before you can even knock, and your heart’s trying to climb out of your chest.
Bobby stands there, cap low, hands stuffed in his pockets. For a moment, his eyes just rest on you. Not in shock. Not in awkward hesitation. But in something warm. Familiar. Like he’s seeing someone he’s been waiting for. He says your name quietly, as if it’s a thing he’s been carrying around in his back pocket for decades.
“Hey, kid,” he says, flashing an almost sheepish smile. “’Bout damn time.”
You exhale a breath you didn’t know you were holding before you think you can speak again. Your hand in Dean’s gives you reassurance. He hasn’t stopped holding it since he picked you up.
“I’m not late,” you quip softly – shakily, your voice wobbling with a smile you weren’t expecting.
“You’re just like your mother.” Bobby chuckles. “Look like her, too.”
You manage a smile, your heart pounding like it could crack a rib. “Yeah, I get that a lot.”
Dean then lets go of your hand as you cross the threshold, but he stays beside you, a palm now resting on the small of your back. The living room smells like leather, coffee, and something fried. It always has. It’s simple and yet perfectly cluttered with books and photos.
You take a seat on the threadbare couch, knees bouncing with nervous energy.
Bobby lowers himself into the armchair across from you, eyes steady. “Been thinkin’ about this day for a long time. Didn’t expect it to feel like this.”
You tilt your head, studying him. “Like what?”
“Like someone finally took the weight off my chest and replaced it with a damn truck.”
You smile softly. “Well, you never were great with feelings.”
“Still not,” he mutters. Then he looks at you, eyes crinkled and earnest. “I know you got every right to be mad. And maybe you should be. But I wanna say it anyway – I’m sorry.”
Your brows draw together. “For what?”
“Hell,” he says, rubbing his palms on his jeans. “Pick one. For the years I stayed in the background. For pretending I was just some guy runnin’ a diner when I wanted to be more. For not tellin’ you sooner.”
“I’m not mad,” you assure him. And you really aren’t – not after the last few days you’ve had. Mostly, you’re just curious. “Not at you. Not at Mom. I get it. I mean, as a kid you always think your parents can do no wrong. But then you become a grown-up and suddenly screw up all the time. Life's pretty damn messy.”
“Ain’t that the truth.” Bobby huffs a small laugh, shaking his head. “So I reckon you’ve got questions, kid.”
“Why didn’t anyone ever tell me?” you ask.
Bobby rubs the back of his neck, his voice gentle. “Your mom and I… it was a long time ago. We were high school sweethearts once. Back before she turned full flower-child and decided California sounded better than Kansas.”
You blink in surprise, a small smile twitching at the corner of your mouth. You share an amused look with Dean over your shoulder, who’s standing near the bookshelf, letting you have your space but still there, steady as a lighthouse.
You know your mother has lived a few years in California from her many adventurous stories. But you’ve always wondered what made her come back to Lawrence.
“Sounds like her.”
Bobby chuckles. “Yeah, she was always wanderin’. Free spirit, that one. After high school, she split for the coast, and I figured I’d never see her again.”
Apparently, you and your mother have more in common than just looks and wit.
“What happened?”
“She came back a few years later. Outta nowhere,” Bobby says, and you can see Dean nodding along like he understands. “But I was already married by then. It wasn’t… right. But it was her, y’know? Love of my life. And for a little while, we were kids again.”
Your heart twists when the realization hits you. “You had an affair.”
His eyes are heavy with something between guilt and acceptance. “It was short. Didn’t mean it wasn’t real. But my late wife, she didn’t deserve that kind of betrayal, even if it was brief.”
“And Mom?”
“She didn’t want to mess up my life,” Bobby replies with a long sigh of regret. “Figured I’d be a better father from a distance than none at all. So I kept an eye out. Paid what I could. Made sure you and her had what you needed. I didn’t know about you. Not right away. I found out when you were a year old. I think she thought she was protecting everyone. You especially.”
You’re still not mad at them, not even at your mother. Even with all her quirks, she’s been a pretty awesome parent. You were never really missing anything. You can’t help but wonder, though, whether the same fate would’ve happened to you and Dean if you’d come back a week later than you did.
It explains why she’s been so hellbent on sending you on a cosmic journey this week – even going as far as risking your driving safety.
You look at Bobby, your eyes stinging with unshed tears, your throat tight. “I remember you coming to my recitals.”
“I sat in the back,” Bobby nods. “Plays, poetry readings, graduations. Every damn one. I was proud of you, even from a distance. You had a solo in that middle school production of Guys and Dolls? I was there. Cryin’ like a baby.”
Somehow, it all makes a terrifying amount of sense. The way he always looked at you a little too long at holidays, but never said much. How he’d just show up at school plays or graduations without a word, a background figure you never questioned – just a friend of your mom's.
Bobby clears his throat. “Y’know… I thought I was doin’ the right thing, keepin’ a distance. Just sendin’ money to your mom when she’d take it. Watchin’ your college graduation from the back. Bein’ there without bein’ there. But I shoulda known that ain’t how family works.”
“Thank you for being there. Even if I didn’t know it at the time,” you say and gift him a smile. “I used to hate not knowing who my father was. I’d make up stories about who he might’ve been. Writer. Drummer. Astronaut. And then my mom would also invent her own stories.”
Bobby laughs a little. “Well, I got some drumsticks somewhere, but I doubt I could keep a beat. I did play the didgeridoo once for your mother.”
You smile back before you mean to. “Crimson and Clover?”
Bobby chuckles warmly. “Yeah, that one.”
Dean glances down at you with that soft, stunned expression that always makes you want to climb him like a tree.
Bobby then leans forward, elbows on his knees. “I’m sorry your mom didn’t tell you. But she was trying to do the right thing in her own way. And I never pushed her to come clean. I figured if you ever came lookin’, I’d tell you everything.”
You glance briefly at your fumbling fingers in your lap. “Are you okay with this? With me being here?”
Bobby smiles broadly. “Kid, I’ve been waitin’ damn near thirty years. This is the best damn thing to happen to me since cable TV started syndicating Bonanza.”
You snort a laugh. “That good, huh?”
“Better,” he says. “You’re family. You always have been. Now we can finally say it. I’m glad you’re here.”
“I’m glad I came,” you say finally.
“I’m sorry for not leaving you the diner, by the way,” Bobby says then, causing your brow to furrow. “Just figured you were already a bestselling author. Probably wouldn’t have use for it. Figured you could do more with the money for whatever you’d need in life.”
You laugh lightly, shaking your head. “Bobby, it’s fine. I mean, me? Running a dinner? My cooking skills are abysmal.”
"True," Dean chimes in, earning him a look from you.
“Yeah, I remember when you worked for me that one summer,” Bobby says, chuckling. “Took you only three days to set the kitchen on fire.”
“Exactly,” you agree, laughing. “Benny was the better choice.”
Bobby’s gaze then shifts to Dean behind you, and something in his face sharpens. “You know,” he drawls, like he’s changing gears, “I remember the first time this idjit came into the diner with you. Hair full of grease. Grinnin’ like a damn fool. Always wanted to impress you. Couldn’t tell his ass from a radiator back then.”
Dean grins. “Still can’t.”
“But,” Bobby adds, eyes narrowing just slightly at the man behind you, “if you so much as breathe wrong around her now, I’ll turn that Impala of yours into scrap and sell the pieces on eBay.”
“What the he–” Dean opens his mouth and closes it again, swallowing thickly. “I mean, yes… sir?”
You snort a loud laugh. “That’s a new level of commitment.”
Dean glances at you then, a smirk playing on his lips. “You gonna defend me, or…?”
You shake your head, leaning back into the couch with mock innocence. “Nope. I’m on Team Bobby right now.”
Bobby finally smiles for real, his shoulders a little looser. “Smart girl.”
He then walks the two of you to the door. Just before you step out onto the porch, he pulls you into a hug – gruff and awkward and perfect. He wraps his arms around you in a way that makes something inside your chest crack wide open. He’s solid. Warm. Real.
You weren’t ready for how badly you needed this.
“Don’t be a stranger,” he says.
“Wasn’t planning on it,” you reply, grinning before the door closes.
Dean walks down the steps, chuckling. “So that was terrifying.”
You roll your eyes playfully. “Coward.”
As you and Dean stroll down the gravel path toward the car, the air feels clearer. Your chest’s a little lighter. The summer breeze catches your hair, the sun sliding low in the sky, casting warm gold across the yard. But before you’ve reached the Impala, you stop walking.
Dean halts as well and turns toward you with a bit of worry on his freckled face. “What’s wrong? You okay?”
You nod slowly, your throat thick. “Yeah, I’m more than okay. I just…” You look at him, your heart too full. “Thank you. For giving me this. For doing this for me. I don’t even know how to–”
He takes a step closer. “You don’t have to thank–”
You don’t even let him finish. Instead, you rise up on your toes and kiss him.
It’s not soft. It’s not hesitant. It’s not maybe or someday. It’s now.
It’s you, choosing him.
Dean lets out a soft sound of surprise, but his arms come around you in an instant and pull you closer. His mouth parts under yours, deepening the kiss, hungry and searing all at once. You gasp into him, and he groans against your lips, one hand tangling in your hair as he presses you back against Baby like he’s been waiting to do this forever.
By the time you break apart, you’re both breathless and dizzy and trembling a little.
“Wasn’t expecting that… yet,” he says, chuckling lightly. “You always wreck me, you know that?”
You giggle. “Right back at you, Winchester.”
Dean presses his forehead to yours. He cups your face, brushing his thumb along your cheekbone. “You ready for the next clue?” he asks softly.
Your brow raises, laughing. “There’s more? You’re insane.”
“Yeah, well,” he says, pulling a crumpled note from his jeans pocket and placing it in your hand, “you’re in love with me, so what does that say about you?”
You unfold the note, heart pounding again as you read the words:
You’re almost there. You always said the stars looked closer from up here. This is where I loved you for the first time (and where I hope you’ll let me do it again). Meet me where we watched the sunrise the morning after we saw that super cool comet, and you wished we could stay like this forever.
You lift an eyebrow, amused. “‘Super cool’? Couldn’t find a better adjective?”
“What, you want me to bust out a thesaurus every time I think somethin’ kicks ass?” Dean chuckles as your cheeks flush with warmth. “‘Cause I will. I’ll get real academic on you. Next time it’ll be… exceedingly badassical.”
You snort a laugh. “This is why you had a C in English.”
“Oh, yeah? You checked the back yet? Wrote a little somethin’ for you,” Dean shoots back, smirking wide. “Thought I could go a little more graphic since I’m the one giving you this.”
As you flip the note around and read, your eyes widen with each word. You almost choke on your spit when you reach the real graphic part. “Wow… I think I’ve never read the word ‘cock’ that much in a paragraph before. Is that a haiku about my–”
Dean outright beams with pride. “Damn right it is. Some of my best work if you ask me.”
You laugh loudly, tears stinging your eyes. You pull him in and press another kiss to his lips. “You’re an idiot.”
“But I’m your idiot, right?” Dean retorts, and you nod keenly, your cheeks hurting from smiling so damn much. “Still with me?”
“Yeah, lead the way,” you reply softly.
Dean opens the car door for you and looks at you like he’s already home, a slow smile spreading across his face. “I’ll drive.”
The Impala crests the winding road with a low rumble, its headlights carving soft yellow arcs through the Kansas dark. The fields below are nothing but shadows now, all blue and velvet, and the moon overhead seems to be doing its best to eavesdrop.
You sit with your shoulder pressed against Dean’s, the soft rumble of the engine underneath you steady, low, and familiar like a heartbeat. One of his hands rests on the steering wheel, the other curled loosely around yours on the bench seat, your knuckles occasionally brushed by his thumb.
It's the kind of touch that says more than words. That says finally, still, always.
“How long have you been driving around with that smirk on your face?” you ask playfully, narrowing your eyes.
Dean glances sideways at you, lips spreading wider. “What smirk?”
“That one. The ‘I’ve got a secret and it’s killing me not to tell you’ smirk.”
He doesn’t even try to deny it. “We’re almost there. Just wait.”
The Lookout is coming into view now, but it isn’t the same shadowy ridge it’s always been. Tonight, it looks like something straight out of a dream.
Fairy lights blink soft and golden across the trees, strung in arcs that sway in the breeze like fireflies on summer nights. There are lanterns tucked along the path, flickering with amber warmth, and a scattering of wildflowers trails the ground – your favorite kind. A blanket is spread across the flattest part of the clearing, anchored with champagne flutes and a food basket.
Dean cuts the engine, and the sudden silence makes it all feel surreal.
“Dean…” you breathe. “What…? When…?”
He’s already grinning. That lopsided, infuriating, absolutely soul-wrecking smile. He looks at you, soft-eyed and proud. “Told you I had one more surprise.”
You step out of the car in a daze, head turning to take it all in. Dean gets out as well, walking around to join you with a smile.
“Had some help. Our moms,” Dean says, scratching the back of his neck.
Your mouth falls open. “My mom did this? With Mary?”
“Jess helped, too. Said she couldn’t resist,” Dean says, chuckling. “Mom and Connie got real serious about it. I told them fairy lights might be overkill and they both looked at me like I insulted their religion.”
“I…” You spin in a slow circle, overwhelmed and awed. “This is… Dean, it’s perfect.”
“Not yet,” he murmurs and steps closer. “But it will be.”
Your heart does something seismic. Almost bounces out of your chest like a kid on a trampoline high on sugar.
Dean takes your hands, and the light caught in his eyes makes them look like a myth from a fairy tale – a little emerald, a little gold, and a little yours. You finally notice it then – he’s nervous. Not cocky, not smug – nervous. Dean Winchester, high school heartthrob and sexiest mechanic alive, looks like a guy trying not to pass out.
As you look at him, he’s watching you and not the lights – not the mesmerizing view of the town you grew up in down below.
“What?” you ask, smiling curiously.
He shakes his head, that soft look never leaving his freckle-dusted face. “Nothin’. Just... trying to memorize this. You know, for the next memory lane trip in ten years.”
You laugh a little. “You planning on making this a tradition?”
“Maybe.” He grins. “But without losing you again. I missed you every day.”
You feel your throat tighten.
Dean clears his throat and lets out a quick, nervous breath. “Okay,” he says, voice lighter, teasing, “so, full disclosure, I know this next thing is kinda nuts.”
You lift an eyebrow, amused. “Define ‘kinda.’”
“I mean, we just got back together, like... what? Ten minutes ago?”
“Eight,” you reply, playing along. “And I’m still deciding.”
“Rude,” he mutters, but he’s still grinning. “Anyway, I know it’s insane. I know we’re still figuring this out, and you probably haven’t even gotten all your stuff from New York, and I didn’t exactly ease into this, but…”
Dean drops to one knee in the grass in front of you. And now, you think you might pass out.
He pulls something small and velvet-black from his jacket pocket. “I’ve spent a lot of years thinking I lost you. And that was on me. Because I let fear talk me out of fighting for what I wanted most. I thought I’d just slow you down. That if I held on too tight, you’d start to see all the cracks.”
Your heart flips and does more gymnastics than you’ve ever done in PE.
“I thought if I stayed in Lawrence and let you go live your big New York life, that somehow it would hurt less than trying and losing you for real. But you know what hurt worse?”
You shake your head quietly, afraid to breathe. Afraid to even blink.
“Watching you leave and not doing a damn thing to stop it. Telling myself I wasn’t good enough and then trying to live like it was fine. I was an idiot. Because the only thing worse than losing you was never giving us the chance.”
He takes a breath and opens the box. Inside sits a ring – vintage, delicate, rose gold, and unmistakably Mary Winchester’s.
Your breath catches. Your ears are ringing, your muscles shaking.
“She wouldn’t give this to me when I was engaged to Jo. Refused. We had a big fight about it, actually,” he says quietly, watching your reaction. “Said that she always meant it for you. I didn’t know what that meant back then, but... I do now.”
“Dean–” You’re at a loss for words again. How many times is it this week? Maybe you should switch careers at this point.
“I want you, sweetheart. I love you. I never stopped and never will. No more maybes. No more what-ifs. No more ten-year detours. Marry me.”
You laugh, stunned, head and heart spinning in circles. “This is crazy.”
Dean grins a little, still rattled by spiking nerves. “I know. But I think we’ve wasted enough time. Don’t you?”
You fall to your knees in front of him and sling your arms around him, crashing your lips to his like it’s the only answer that matters. When you finally pull back, breathless and happy, you whisper against his cheek, “Yes. Yes. And yes.”
Dean exhales a long, shaky breath, one that sounds like it waited a decade to finally let go. “You sure?”
You nod vigorously. “Yes. Never been surer about anything.”
He laughs, bright and boyish, and sweeps you up in a kiss so soft it makes the universe feel quieter – at peace.
“There’s something else,” he says then, causing your brow to wrinkle in amusement.
“Don’t you think you’ve thrown enough life-changing events at me today?” you tease, giggling.
Dean snorts, but he’s nervous again. “Yeah, well, this one wasn’t exactly my idea,” he starts, clearing his throat somewhat awkwardly. “But, uhm, as you know there was supposed to be a wedding tomorrow. Our moms might have banded together and replanned it. You know, stuff they thought you like. Dresses, flowers, even pie instead of cake. So… if you want–… if you want me – we can get married tomorrow.”
“Wait, wait, wait.” You have to laugh a little. “You want to marry me tomorrow?”
He shrugs one shoulder. “Yeah, bold move, huh? But listen, only if you want to. If it’s too fast or too weird, we wait. We wait a year if you need it. Ten. I’ll be here, no matter what.”
You bite your bottom lip for a moment, but you can feel yourself already nodding before you blurt out your answer. “Yeah… Yes! Let’s do it! Let’s get married tomorrow.”
Dean cocks an eyebrow like he hasn’t expected that answer. “For real?”
“Yes,” you assure him and peck his lips, cupping his cheeks. “There’ll never be a different answer as long as you’re the one who’s asking. You were always it for me, Dean. End game. I love you, okay? I never stopped, either.”
A chuckle rumbles through Dean’s chest that sounds like relief before his eyes twinkle with a familiar hint of mischief, his forehead pressed against yours. “So, what d’you say we finally make Baby’s backseat our last stop on the tour?”
You snort a small laugh, cheeks pink. You teasingly brush your nose against his, musing. “Hmm, I don’t know. Might as well wait till the wedding night.”
“Seriously?”
“Yeah, seriously.” Your lips brush his, all smiles underneath. “But you might convince me to go as far as third base again.”
“Done,” Dean says and claims your lips in the same breath, pushing your back down into the grass, your giggles echoing into the starry night.
The sky stretches above you in a soft haze of stars, the kind you only see in towns like this – quiet, steady, a little drunk off summer.
You’re curled into Dean in the backseat of the Impala, barefoot and a little windblown, the white lace hem of your flowy hippie-style wedding dress tangling around your ankles like ivy, catching on the gearshift and the door handle and the loose change in the floorboards. Wildflowers still stick stubbornly in your hair, most of them from your wilting crown. Your cheeks ache from smiling too goddamn much today.
Dean’s arm is slung around your waist, his hand resting over your belly, fingers twitching now and then like he’s still in disbelief you’re here – real, warm, his. His other hand is absentmindedly toying with a frayed bit of lace near your knee.
His boutonnière is long gone – lost somewhere between the vows and Cas tackling him in an emotional hug afterward. His hair is tousled, his smile easy, and a streak of your lipstick faintly smudges along his jaw. His white dress shirt is wrinkled and untucked, his sleeves rolled up, the top buttons undone. Your mom has even stolen one of his old flannels that you still kept in your closet and sewn him a tie out of the scraps. His jeans hug his bow legs perfectly – and yes, you married a man in jeans. Because of course you did.
You can hear the music faintly from the bar down the hill – Rocky’s is still alive with what remains of your wedding party. The last-minute reception has gone exactly how you’ve imagined it would go if both your moms were given twelve hours and no rules: haphazard, heartfelt, and absolutely perfect in an unhinged way.
You exhale into the quiet, cheek pressed against his shoulder. “I think your mom tried to kill me with love today.”
Dean lets out a low, contented laugh. “Yeah, she was real happy. But I think most of it was just the mushrooms.”
You groan. “God, right. My mom drugged the entire reception.”
“Just a little,” he says, mock-defensive and chuckling. “Microdose. Functional dosage. Her words. Honestly, if you think about it, it was really sweet.”
You arch an eyebrow. “You think my mother spiking the punch like a chaotic teenager is sweet?”
“Hey, she made sure we didn’t get any. Just wanted everyone occupied, so we could sneak away. Told me ‘no bride, no groom, no pregnant ladies.’ Said she was designated chaperone. Blocked me and Jess before we even got close to it. Almost tackled me to the ground, too. It was disturbingly thoughtful,” Dean says, ever the defender of your mother’s shenanigans.
You giggle softly. “She’s scary when she wants something.”
Dean snorts. “Yeah, she wanted us to get laid. Which again – disturbingly thoughtful.”
“Guess so,” you laugh and bite your lip. “I’m still wondering if Cas even blinked once while he was officiating us.”
Dean gave a low laugh, chest rumbling under your cheek. “Nope. He was dead serious. But Charlie balanced it well with her toast.”
“Oh God, don’t remind me. I still can’t believe she opened with, ‘Once upon a time in the backseat of a Chevy Impala…’”
Dean grins. “To be fair, she warned me she was gonna say something inappropriate.”
You nudge him playfully with your shoulder, laughing again, quieter now. “She meant it, though,” you say softly. “They all did. Even Bobby. You saw him tearing up when he walked me down the aisle.”
“Not just Bobby,” Dean huffs, amused. “You made everyone cry with your goddamn vows. Even my dad was bawlin’ his eyes out. Don’t know how you pulled that off. You had, what? Three hours to write that thing? Sounded like it came straight outta one of your novels.”
You smirk and give an innocent shrug of your shoulders. “I’m a writer. I had to go for the emotional sucker punch, okay?”
Dean snorts under his breath and kisses your temple, the wedding band around his finger catching in the light. “Well, mission accomplished, sweetheart.”
You’re both quiet for a heartbeat, letting the memory of your wedding hang there. Your mom buttoning your dress with shaking fingers. Sam walking down the grassy aisle with Jess holding his hand. John tearing up on three separate occasions. Meg waddling to the buffet like a queen, heavily pregnant and still rocking four-inch wedges – she insisted on coming, even though she’s a week past her due date. Benny hooted the loudest when you kissed Dean during your first dance. Mary created an amazing food spread again. Kevin tried to DJ from a laptop while Garth spun his wife around the pool table.
Your people. Your strange, perfect little world.
“You okay?” Dean breaks the comfortable silence first, nose brushing your hair.
“Mm-hm,” you manage to hum in total post-wedding bliss.
“Tired?”
“Mm-hm.”
“Happy?”
You glance up at him, your heart warm like your holding the entire sun hostage in your ribcage. “So happy it feels fake.”
He smiles at that – soft, crooked, and a little tired too. “You’re my wife now,” he says like he’s still trying to process it.
You beam. “You gonna start calling me Mrs. Winchester in bed?”
“Only if you call me Mr. ‘Yes, right there – don’t stop.’”
You laugh – genuine, loud, and peaceful. “God, we’re such trash.”
“Legally married trash.” Dean grins.
He kisses you again, this time on the mouth – slow and lazy, your favorite damn kind. His lips taste like champagne and cherry wedding pie and something saltier underneath – sweat, effort, realness. You melt into it for a moment before pulling back with a quiet sigh.
“So, what now? Do we just go home?” Dean asks, making you giggle.
“Uh, I mean… Am I moving into your place? I still have to get all my stuff from New York,” you note, realizing how ridiculous it sounds saying that to your husband.
Dean laughs at that, rubbing his jaw. “Right. Guess we’ll do that then.”
“I have a cat.”
“I’m sorry, what?” Dean blinks down at you. “Usually something you tell a guy first before gettin’ married. Especially if the guy’s a dog person.”
You snort a giggle. “We can get a dog, too. We can fill the house with a whole sitcom cast.”
“Alright, what’s the judgmental asshole’s name?” Dean jokes with a teasing grin.
“Hemingway.”
His smile broadens. “Actually did it, huh?”
Your brow raises. “You remember that?”
“Yeah,” Dean says like it’s obvious and shouldn’t be questioned. “I think I’ve proven enough this week that I remember everything that concerns you.”
“True. You did,” you reply, smiling.
“Guess I’ll have to get used to cat hair on my couch,” Dean quips.
“Your couch?” You cock an eyebrow, grin still present.
“Our couch,” Dean corrects and pecks the top of your head.
“You know, I already have ideas on how to spruce up the place a little,” you say with a teasing edge in your voice.
Dean groans, head falling against the backrest. “Jesus Christ, there are gonna be millions of books stacked everywhere, aren’t there? Gonna look like that apartment you shared with Charlie during college. Your tea collection is probably gonna take up the entire pantry.”
“Don’t forget to share your closet space with me, too.”
Dean chuckles, fingers lazily brushing your waist. “So, what? Road trip to New York for our honeymoon to get your stuff? Haven’t even planned anything yet.”
You contemplate for a second before a slow smile forms on your lips. “Let’s make it a whole trip. Go for a month. Like old times. Cheap motels, awful coffee, greasy diner food, seedy dive bars, and gas station snacks. We could chase bands and weird tourist traps.”
Dean looks at you as if he isn’t sure he’s not dreaming. “You serious?”
“Yeah, you drive and sing along to Zeppelin while I ride shotgun with my notebook. Just you, me, a pen, and the open road, baby.”
Dean blinks at you only for a second before kissing you reverently. “God, I love you.”
You giggle softly. “Good thing you put a ring on it then.”
“Best decision I ever made.”
“You know, Bon Jovi and AC/DC are on tour right now. We could see them,” you suggest, your mind already mid-honeymoon planning.
“I wish. Tried getting tickets months ago. No chance,” Dean sighs with full disappointment.
But you wave it off. “Oh, it’s no problem. I know a guy. Just have to make a call.”
Dean’s brow shoots up. “What? You just happen to know a guy who can give you tickets to the greatest rock bands that ever lived?”
You twitch your shoulders. “I mean… yeah? I’m a bestselling author now. I meet a lot of people at events. And that guy works in the music industry and still owes me a favor. I signed a copy of one of my books for his daughter. She’s a big fan.”
“Huh.” Dean stumps for a second. “Really did marry well…”
You swat his chest playfully, chuckling.
Dean looks down at you then, that familiar, boyish smirk spreading on his lips. He reaches out and tucks a strand of hair behind your ear, his thumb lingering on your cheek. “You know, before we fully go planning the honeymoon, there’s still one more thing on our list.”
You’re already smiling when his fingers brush up your thigh. “Oh?”
“Mm-hm,” Dean hums and slowly presses you into the backseat, lips trailing down your throat now. “Something we haven’t done in… ten years?”
“Hmm… And what could that possibly be?” you play along, your fingers already wandering down his chest, legs spreading wider to accommodate his hips. “You know, I learned a few new tricks.”
Dean smirks. “Did you now?”
“Courtesy of my mother,” you quip, but it’s not even a lie. “She gave me a sex book for every birthday over the past decade.”
Dean snorts, lifting a brow. “And you actually read ‘em?”
“They’re books, okay?” you defend with red and burning cheeks. “I can’t just have them lying around and not read them. My mother knows my weaknesses.”
Dean’s mouth is already on yours before you can finish laughing. His hands find your waist, your thighs, pulling you closer, closer, and closer. It’s messy and beautiful. Most of all, it's long overdue. It’s the kind of kiss that makes your knees ache and your spine melt and your lungs forget what they’re for. The kind that rewrites a decade of silence and stubbornness and heartache.
Outside, the twinkling stars above keep watch. But this isn’t just the end of the night or the end of a book. Luckily, this is only just the beginning – the first chapter of a brand new story.
🎬 The End
What did you guys think of this ending? Did Dean earn his forgiveness? That scavenger hunt was such a cool thing to plan and write. I loved including all their friends and family. I'm honestly so in love with this ending 🥰
Let me know if you ever want a little bonus one-shot of that wedding night 😉 Or maybe something from their honeymoon? I kinda miss them already lol 💕
Tag List Pt. 1:
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