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hearteyes-j2

Feb 15, 2025

janicho88

Know When To Let Go Part 1

Pairing- Dean, x Female!Reader.

Word count- 3,889

Warnings- A lot of ANGST, Dean is a bit of jerk, fighting,

Summary- You almost lost Dean to a heart attack, now after one phone call there is another threat from the past that could come between you two.

A/N-I know this isn't one of my ongoing series, but this has been in my drafts for years. The first 2 parts are a rewrite of the Route 66 episode. I'm trying to get back into writing, I promise. It's been so long since I've posted, I'm not even sure what to use for a taglist so I'm going off the last Forever tag list. If you would like to be removed let me know. Not Beta'd, all mistakes are mine

Sitting in the back of Baby, you think back on this last week, it was one of the worst of your life. During the last hunt Dean had been electrocuted which led to him having a heart attack. Doctors didn’t give him much time, you and Sam worked like crazy looking for some way to save him. Finally, Sam found a faith healer, which turned into another case on its own. Now, Dean was in the motel room saying goodbye to the chick he met on this job. Sam was kind enough to bring her back to talk to Dean. No, you weren’t jealous at all, but does he seriously have to meet a girl in every town you stop in?

Your parents had been hunters and would drop you off at Bobby’s, which is where you met Sam and Dean as kids. Dean was a year older, and had taken you under his wing. When you were twelve, your parents never made it back from a hunt. You lived with Bobby until you turned 18, then you started hunting with the Winchester instead of researching at Bobby’s. Sam was like a little brother to you, even if he shot up taller than all of you. Dean was your best friend and as you grew up, he was the man who stole your heart. You never saw him sharing those feelings so you kept them bottled up. This left you standing by and watching, the constant hookups and flirting breaking your heart a little more each time. Sam has known since you were kids there was something between you and Dean, and often pushes you to tell his brother. You could never bring yourself to do it, and in turn, lose Dean altogether.

You were there for Dean through everything, the rough hunts, Sam leaving for Stanford, fights with his dad, then John disappearing a few months ago which led to picking up Sam who then lost Jess. You couldn’t imagine what losing Dean last week would have done to you. When he was in the hospital, you came close to telling him how you felt when he was holding you next to him in the tiny hospital bed. The two of you had gotten fairly close over the last case, but once again someone else had caught his eye.

The three of you stop at a gas station when Dean gets a phone call and walks off. Sam is standing next to the car looking over a map to plan your route to Pennsylvania, where your next case is. Dean starts heading back to the car putting his phone away.

“I think I found a way we can bypass that construction just east of here. We might even make Pennsylvania faster than we thought,” Sam calls out.

Dean looks out over the car before turning to the two of you, “Problem is, we’re not going to Pennsylvania”

You and Sam look at each other before looking at Dean. “Where are we going then?” You ask.

“I got a call from an, uh, old friend. Her father was killed last night, thinks it might be our kind of thing.”

“What? Who’s the friend?” Sam wanted to know.

“Listen, trust me on this, she never woulda called, never, if she didn’t need us.”

There is a sinking feeling in your stomach, “who is the friend Dean?” He just ignores you and hops in the car.

As you were driving Sam again tries to get Dean to tell him who the old friend is. You are headed to Mississippi, which gives you a pretty good idea of who this friend is and you are livid.

Dean finally says the name you are dreading, Cassie. You had been traveling with Dean when he met her in Ohio, and they had gone out for a few weeks. You didn’t like her then and you really didn’t like her the night Dean came back to the hotel drunk and heartbroken because she ended things. She was a stuck up snob, she absolutely crushed Dean.

“She actually had the nerve to call you and ask for help?” you exclaim. Unfeaking believable, and apparently Dean is still pretending he can’t hear you.

“You never mentioned her before,” Sam is telling Dean.

“Really?” When Sam just looks at him Dean continues, “ Yeah, we went out.”

“Like more than one night? You actually dated somebody?”

“What are you not getting here? Dad, Y/N, and I were working a job in Ohio, she was in college.

We went out for a couple of weeks.”

“What happened between you guys?”

“Drop it Sam,” you really didn’t want to dig up this part of the past.

“Was there more going on?” The dense man kept pushing.

“Yeah, they went out. She was a bitch, they broke up, it broke his heart, and I had to fix her mess.”

“Knock it off, Y/N. That was years ago, and in the past.” Now he acknowledges you, just to defend her. He couldn’t still have feelings for her could he?

“Okay. So I’m sorry about her dad, but why would she call you if he was in a car accident? Not really our kinda thing?” It took Sam a minute, “wait, does she know what we do?” Dean didn’t answer staring ahead. “Dude, you didn’t?”

“He actually told the bitch what we really do, Sam.”

“Watch it Y/N.” Dean gives you a glare through the rearview mirror, and you give one right back.

Sam looks at you curiously. You aren’t usually one for hate unless they deserve it.

“Wait. You told her. You told her our secret! Our big family number one rule, we do what we do and we shut up about it. I never said a word about it to Jess for over a year and a half, instead I lied to her. But you tell some girl you only knew a few weeks, everything.” Dean still didn’t answer, just looking straight ahead. “Dean!”

“Yeah, looks like.” He just pushed down on the accelerator ignoring Sam’s bitchface.

“Witch, didn’t deserve to know anything,” you muttered under your breath. Judging by the glare Dean sends back he still heard you.

There isn’t much talking between any of you after that. You arrive in town and Dean parks near the newspaper building and quickly exits the car. Guess she told him where she works.

Walking inside you see three people arguing and unfortunately recognize one of them as Cassie. One of the men leaves and the other walks away when Cassie turns to face the three of you, giving Dean a grin and calling out his name. Dean gives her a small grin. Why is she so happy? She's the one who dumped him. Oh she just made you fuming mad.

“Hey Cassie.” She doesn’t say anything and they just stare at each other before Dean continues. “This is my brother Sam, and you remember Y/N.”

You would be pretty shocked if she didn’t remember you. After calming Dean down and he finally passed out that night, you went to her apartment and bitched her out. Which is probably why she smiled at Sam and ignored you.

“I’m sorry bout your dad,” Dean started.

“Yeah, Me too,” she answers.

Well, she does talk. This staring is driving you nuts. “You called Cassie, apparently you think you need our help.”

“I didn’t know you would still be around.” She quickly glances at you before going back to Dean, “Maybe we should go somewhere else.”

“Well, I don’t desert the people I care about.”

Dean glares at you as everyone leaves the building and walks back to the Impala to follow her to her mother’s house. When she gets in her car Dean grabs your arm stopping you. “That’s enough out of you! You don’t have to be such a bitch, you know.”

He climbs behind the wheel of Baby, and you roll your eyes before sliding in yourself.

Cassie brings out tea when you arrive, she settles down close to Dean. She tells you all how her mother has been in bad shape, so she was staying at the house with her. She has been very nervous lately and worried about her husband. When Dean asks why, Cassie mentions her dad had been scared and seeing things, like an awful-looking black truck following him. Sam interrupts to ask who the driver was, but apparently her dad never mentioned one. The truck was always appearing and disappearing. Her father’s car had been dented in the accident, and it looks like something big.

You’ve been watching Dean, and have to hide a laugh when he is giving his tea a weird look before quickly putting it aside on the table. You turn your attention back to what Cassie is saying. The sooner you solve this, the sooner you can leave this town.

“Dad sold cars, and was always driving a new one. There wasn’t a scratch on it before the accident. It was raining hard that night, and mud was everywhere. There was one distinct set of muddy tracks which led from dad’s car to the edge where he went over.” She paused trying to gain control of her emotions, “only his tracks.”

“The first accident, he was a friend of your father’s?” Dean asks her.

“Yes, Clayton Soames, they were best friends, and owned the dealership together. Same thing, a dent, no tracks, and the cops said he lost control too.”

Dean wants to know if she has any thoughts on why the two men would have been targets, but she doesn’t. Then Sam asks her if she thought it was the vanishing truck her dad saw.

“When you say it out loud like that, listen, I’m a bit skeptical about this… ghost stuff… or whatever it is you guys do.”

“Skeptical? If I remember right you said I was nuts.”

“If you don’t believe it, why did you bother calling Cassie?” You cut in after Dean. Getting another glare from the man.

“That was back then, I just can’t explain what happened so I called you.” Her and Dean are back to staring at each other, I just might be sick you think.

“Excuse us a second,” Dean gets up and grabs your arm, pulling you out of your seat across from him and to the corner of the room. “If you aren’t actually going to be any help you can leave, and go wait in the car.”

Before you can reply, Cassie’s mom walks in and she gets up to talk to her. Dean walks away leaving you standing alone. She introduces Dean as a friend from college and Sam as his sibling, you get nothing. Sam sees you hurry outside trying to hide the tears in your eyes, he knows Dean’s behavior has to be getting to you. Excusing himself he follows you outside.

“Sam, you are always telling me I need to be honest with Dean about my feelings. This is why I can’t, he’ll choose some chick who hurt him over me, the person who has been there for him for over 15 years.” Dean comes out and you turn away from him quickly.

“I don’t understand what your problem is, but that was unnecessary,” he snaps at you.

The three of you head back to the motel shortly. It is a quiet ride back, you and Dean aren’t speaking to one another, and Sam doesn’t want to get either of you going. Usually, you share a bed with Dean, but that isn’t going to happen tonight. At least the room has a couch, as bad as it looks it is still better than the floor.

Early the next morning Dean’s phone rang waking you up from the little sleep you had gotten. It’s Cassie, apparently someone else died during the night, same way as the others. Dean is hurrying both you and Sam to get ready and out the door. When you arrive at the scene Cassie is talking to one of the men from yesterday. Dean is quick to walk over, you and Sam following behind.

“Did the cops check for additional denting on Jimmy’s car, see if it was pushed?”

The man looked at Dean then back to Cassie, “Who is this?”

“Dean and Sam Winchester, and… his friend Y/N, they’re family friends. This is Mayor Harold Todd.”

“There is one set of tracks, just one. Nothing points to foul play here.”

“Mayor, the police, officials, everyone is taking their cues from you, if you are indifferent about this then..”

“Indifferent!” He interrupts her

“Mayor, would you close the road if the victims were white?”

“Are you suggesting I’m racist Cassie, I’m the last person you should talk to like that.”

When Cassie tries to find out why, he just tells her to ask her mother and walks away.

From there Dean drives you all back to the motel room to change into fed clothes. While in the bathroom getting ready you can hear the boys talking, well Sam at least trying to get information from Dean about Cassie

“I’ll say this for her, she’s fearless,” Sam starts, Dean just humming. “I bet she kicked your ass a few times. It’s interesting you guys never look at each other at the same time. You look when she isn’t and she checks you out when you aren’t. It’s an interesting observation you know, in an observationally interesting way.”

Just shut-up about her Sam, you think to yourself. “You think we might have more pressing issues here?” Dean finally responds.

“Hey, if I’m hitting a nerve.”

“Y/N, hurry up we’re leaving, let’s go,” Dean yells for you.

You leave for the docks to talk to a few guys who are friends of the victims, Cassie has mentioned they would be there having lunch.

“Excuse me. Are you Ron Stubbins?” You asked, reaching the two men first. When he nods, Dean takes over talking.

“You were friends with Jimmy Anderson?”

“Who wants to know?” Ron counters.

“We’re with Mr. Anderson’s insurance company, got to dot the I’s and cross some T’s.”

“We were just wondering if the deceased had mentioned any unusual experiences recently?” Sam cut in.

The men are looking at the three of you funny so you step in, “Well visions, hallucinations. It’s part of a medical examination kind of thing. This is all standard.”

“It takes three of you to come down? What company did you say you were with?”

“I’m new, these guys are training me.”

“All National Mutual,” Dean cut in. “Can you tell me, did he ever mention seeing a truck? A big black truck?”

“What the hell are you all talking about? You even speaking English?” Ron asks.

“Son this truck, is it a big scary monster looking thing?” The man with Ron cut in.

“Yeah, actually, I think so.” Dean answers him. The man just nods. “What about it?”

“I’ve heard of a truck like that,” he finally answers..

That gets Sam’s attention, “You have, Where?”

“Not a where, but a when, son. Back in the ‘60’s there was a string of deaths. Black men. Story goes they disappeared in a big, nasty, black truck.”

“Did they ever catch the guy?” Dean wants to know.

“No, never found him. Hell, not sure if they even really looked. See there was a time, this town wasn’t too friendly to all its citizens.”

“Thank you for your time,” you tell the men as the three of you turn to walk back to the Impala.

The guys start talking while you follow behind.

“This truck,” Dean starts.

“Keeps coming up doesn't it?” Sam fills in.

“You know, I was thinking. You heard of the flying dutchman?” Dean asks his brother.

“That ghost ship? It was infused with the captain’s evil spirit, and basically part of him.”

“What if this is like the same thing here? You know, a phantom truck, an extension of some bastard’s ghost, that is re-enacting past crimes?”

“Could be, the victims have all been black men.”

“It’s more than that, everything seems to be connected to Cassie and her family.”

“It’s all, all about Cassie,” you mutter under your breath, but apparently not low enough again.

“What is your deal?” Dean turns to you, “you have been a nag ever since I told you we were coming here! All these stupid little comments. What the hell is your problem?”

“You really have to ask me what my problem is? You are so blinded by what you once felt for her. I was there with you Dean, when things ended, I know how much she hurt you. I absolutely hate her, and so did you before yesterday.”

“She hurt me, me, not you. I never asked for you to help me, it’s not up to you how I handle this. My life doesn’t concern you, stay out of it! Grow up Y/N, I’m sick and tired of your attitude.”

“Maybe it’s just time I did get out of it. If I’m gone then I can’t interfere in your life anymore.”

“Maybe that would be a great idea. I’m over the way you’ve been lately.”

“Fine, after this case, I’m out of your hair.”

“Best thing you’ve said all case.”

“Alright guys, let’s just calm down,” Sam tries to intervene before it blows up, turning to Dean, “you go work that angle with Cassie and her family, talk to her”

“Yeah, I will.” Dean throws a glare your way when he answers.

“You might also wanna mention that other thing.”

“What other thing?”

“The unfinished business between you two. Dean, what is going on between you?”

You can’t listen so you walk away to calm yourself down.

“Maybe, we were a bit more involved than I said before.” Sam just stares at him. “Okay so a lot more. I told her our secret, what’s out there and what we do. I shouldn’t have.”

“Come on man, everyone needs to open up to someone at some point.”

“No, I don’t. It was stupid of me to get that close. Just look how it ended.”

“Is that what’s wrong with Y/N? How bad this thing ended with you and Cassie?”

“I don’t know what the hell her problem is, but she needs to get over it fast.”

“Did you love her?”

“Y/N? She’s my best friend, dude I can’t.”

“I meant Cassie, but good to know your mind goes there first.”

“No, didn’t. I’m leaving.”

“You did love her, and you dumped her.” Sam watches Dean for a minute, “Wait, she dumped you?”

Dean walked over to the Impala’s door, “Just get in the car, get in the car.”

“What about Y/N?” Sam asks, getting in and looking around for you.

“She can walk back, maybe it will cool her down.”

You walked around the corner trying to calm yourself down and keep the tears at bay. When you are turning to go back you see the Impala speed by. They seriously left you here? Dean really did want you gone. Looking down, you are glad you didn’t grab the heeled shoes, at least this pair wasn't awful for walking.

You turn back around and start the thirty minute walk to the motel. This time you can’t stop the tears from falling. You have loved Dean for years, and been his best friend even longer. You want to be there for Dean. You were best friends, wasn’t that how it was supposed to be? If you are honest with yourself, you would know it was more than that, he was it for you. It was clear lately, you're not the one for him. Apparently you mean nothing to him. Years ago, when he was hurt by Cassie, he changed and didn’t let anyone, even you get as close as he used to. Maybe you should get your own room tonight, and start adjusting to being on your own. This case couldn’t wrap up fast enough for you to get out of this town.

You arrive back at the motel and the Impala is nowhere to be seen. Either they aren’t back yet, or Dean dropped Sam off and went to her. Heading to the room you plan to grab your things and get another room. Opening the door you think you are alone, until Sam walks out of the bathroom.

“Y/N, I’m glad you’re back, I’m sorry Dean left without you.”

“Don’t worry about it Sam, he obviously isn’t.

”

“What is going on with you two?”

“I think we have just had enough of each other.”

“It’s more than that.”

You let out a sigh before turning to sit on the bed. “Dean doesn’t think straight around Cassie, he never has. I don’t want to see him hurt again, because I know she will. He changed the minute he got her call.”

“When are you going to tell my brother you are in love with him?”

“I’m not Sam, I told you last night, he doesn’t share those feelings. Hell, he wants me gone, out of his life, and maybe that isn’t a bad idea.”

“What are you saying?”

“Our friendship is barely hanging on by a thread, I’m not going to cut that final one by telling him how I feel. He wouldn’t wait for this case to even be over before he made me leave. It’s clear I’ve overstayed my welcome with you two.”

“No, you haven’t. I think we all just need a break after this. You and Dean aren’t thinking straight right now.”

“I’m going to grab another room. I don’t think we need the three of us in one tonight.”

“You don’t need to do that.”

“It would be better if...”

“No,” Sam cuts you off, rubbing the back of his neck. “I’m sorry, but Dean is with Cassie, we need to figure out how this relates back to her family. I don’t know when he’ll even get back tonight, so don’t worry about another room. Everything will be back to normal in a day or two.”

“Sam, I’m leaving when this case is over. I need to be on my own for a bit. You will always be my not so little, little brother, but I can’t stay around him anymore.

Y/N, come on. It’s just a fight, you guys will be fine in a few days.

“I’m going to hit the shower.” You don’t want him to try and talk you out of this decision.

Walking into the bathroom you quickly turn on the water so Sam won’t hear you cry. After 18 years of friendship this is where you finally part ways from the man who has been there for you since he was 8 years old. Dean doesn’t want you around and you can’t keep watching him sleep with all those other women. The knife in your chest twists a little more every time. Getting out of the shower you get ready for bed, sleeping on the couch again because you couldn’t bring yourself to sleep in the bed that smells like Dean, even if it would be the last time. You know Sam is asleep and you don’t fight the tears that surface once again.

Part 2-coming soon

Thank you for reading!

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