Five Conversations Dean Winchester Never Had

AU fic: if Jess Had Never Gotten Pinned To That Ceiling


He's blasting AC/DC out the windows on his way back from New Orleans when he gets the call.

Dean glances at the number before he answers, and stares. Has to slam on the brakes a little hard when he sees the yellow light ahead of him. Turns down the cassette. Takes a deep breath.

Flips open the phone. "Hello?"

"Hey, Dean, it's Sam."

And Dean hesitates, has to figure out how to answer that. Sammy, how's it going!? Dude, great to hear from you, it's been a while! 'A while' being two years and three-odd months because Dean's not keeping exact time on account of that being obsessive. "Yeah, man, I know," is what comes out of his mouth. "Caller ID, remember?" And he could smack himself and give himself a high-five at once for that one, skipping right over the awkwardness of long silence with the mouth of an asshole. "What's up?"

He hears that little snort of breath on the other end and can see Sammy's expression, that rueful yeah, that's my older brother, and isn't he a jerk smile on his face as he shakes his head. "This a bad time?" Sam asks.

Never, Dean thinks. He would have given an arm and a leg to talk to his brother, but getting the voicemail thirty times and thirty days in a row was a pretty resounding door being slammed in his face, and Dean can take a hint. Right. No interrupting Sammy while he's playing 'normal'. "No, no, I'm just drivin'," Dean answers, nonchalant. "Headed up to Ohio. Been in New Orleans. Heh …" he can't help the grin that spreads across his face. New Orleans is full of bad shit, but damn if the city doesn't give as good as it gets, between the bars and the women.

"Dad's in the car?" Sam asks, sounding a little wistful, maybe nervous. Maybe hopeful? It's hard to read.

"No," Dean says cautiously, not sure what reaction he's going to get. Sam couldn't possibly want to talk to Dad, could he? Was Sam finally going to be the one to extend the olive branch? Was that what this out-of-the-great-blue-sky call was about? Don't get carried away, Dean, he thinks ruefully. If he's right, the next word out of Dean's mouth will be 'Christo'.

"Good," Sam breathes, and Dean breathes out too, caught between disappointment and confusion. "Listen, Dean … I'm sorry about … not keeping in touch. I just—"

"Dude, don't hurt yourself tripping over your tongue," Dean warns, warding off the ball of frustration in his chest. Jesus, he can't concentrate on the road at all; he resolves to pull off at the nearest gas station. He doesn't want to hear Sam's apology or excuses; he's calling now, and that's what counts. And it wasn't to apologize, because that's not Sam's style. "Come on, don't leave me hanging here. What'd you call about?" He spies a gas station on the other side of the next light and pulls in.

He hears Sam take a deep breath, an anticipatory breath, the breath right before you have to hold it so you don't give away your position to the powries around the corner.

"I'm getting married," Sam says in a rush.

* * *


Don't tell Dad, Sam had begged. He'll probably show up and ruin it just for spite.

Are you fucking nuts? Dean had shot back. Dad'll be proud. And he sure as hell hoped he hadn't been lying about that one.

Because what he hadn't said, still reeling from the shock that little Sammy had a girlfriend – no, a fiancée, which was a girl with a rock on her finger – was that Dad would be proud, but he'd also be betrayed.

Probably just as betrayed as Dean felt. Maybe more.

It's tempting to take the coward's way out – to call Dad and break the news over the phone, come what may. He'll be home tomorrow if he drives without stopping, and maybe by then Dad will be over the surprise enough to see it was inevitable (damn it) and welcome Sammy's new commitment with open arms.

And tomorrow he'll wake up in Lawrence, four years old again, and this will all be some fucked-up dream.

He plays the conversation in his mind, starting with the opening salvo. Hey, Dad, I'm back. Yeah, the hunt went fine – fine as the women down there. Heh. Hey, Dad, Sammy called me … He's getting married.

His father would look up at 'Sammy', eyes already full of warning. Dean's not allowed to bring Sam up without Dad opening the door for that conversation, which usually starts Swung by Palo Alto couple days ago and ends two sentences later with Sammy's fine. Listen, Caleb called …

Dean tries to imagine how Dad will react to the word 'married', and finds he can't get any further along.

In the end, it doesn't even matter. Dean returns to an empty motel room and no note, nothing to explain it – and Dad's not answering his phone. So he checks all their contacts; Caleb says something about Jericho, California, and Dean thinks there are no coincidences. Maybe Sam called Dad after all, and Dad found a job that would take him close, close enough to pretend Palo Alto was just a stop along the way.

But Sam wouldn't call Dad. So Dean does, picks up the phone and listens to the voicemail again. This is John Winchester …

"Dad, it's Dean," Dean says, like just saying 'Dad' wouldn't give away his identity. There's only one son John ever talks to. "I heard from Caleb you're going to Jericho. Uh … Sammy called. Heh, crazy, right? I can hardly believe it. Anyway … he called because he wanted to tell m—us that he's …" he hesitates. Spit it out, his father the drill sergeant says in his head.

"Look, just call me back when you get a chance, okay?" Dean says. "I'll talk to you later."

He hangs up, and he's not entirely certain if he took the coward's way out or the brave's.

* * *


Dad doesn't call back.

Dean mopes around the motel room for a day before giving up. Sammy's given him an opening, and he'd be stupid not to take it. So he calls Dad and tells his voicemail where he's going, packs up and makes tracks south and west, a beeline to Palo Alto.

He gets there four days later, on Halloween, and Dean reflects that Sam has terrible taste in timing, announcing his wedding plans two weeks before That Anniversary. No wonder Dad's not calling Dean back; it's the second year in a row that Dad's dropped off the map for a week around this time, like it's gotten so bad that he can't even see his son for fear of seeing Mom there too.

Dean knows it's nothing personal, but it makes his knuckles go white around the Impala's steering wheel anyway.

On the way, he works on making his own peace. It's been four years since Sammy stormed out of Dad's life, and two years since he shut Dean out as well. And Dean would never tell Sammy, 'cause it would bruise his fierce, stubborn, stupid pride, but Dean had been hoping for Sammy's call these last few months. He should have graduated in May (not that he told them), so the college life is over, right? Maybe Sam would finally be done running, would finally have made his peace with 'normal' and would be ready to get back to where he belonged.

He wasn't expecting the fantasy to continue into forever – into a wife and two-point-five kids and a dog, a white-collar job and a three-story house in Suburbia, USA.

Once, while delirious from infection and drunk on the Jack Dean had fed him for the pain, John Winchester had said never meant for you boys to live this life. Just wanted you to be safe. And Dean had thought that was absurd. They may not have been born for this, but they had been made for this: saving people. Hunting things. And thinking that 'normal' was possible when you knew what went 'bump' in the night? Was deluding yourself.

But Sammy's bound and determined to try, and even if John is going to give Sammy the silent treatment (and while he's at it, Dean), Dean owes it to Sammy to let him. The way he sees it, he realizes when crossing the border of Nevada, Sammy's too stubborn for his own good, and that leaves Dean with two choices: fight Sammy tooth and nail for his decision and get shoved out again, for good this time, or let him live his fantasy and get to participate, at least a little.

He knows Sammy's apartment number because he read it in Dad's journal, so he parks outside it and stares. It's cute. Quaint, even. Not quite white-pickett-fence material, but collegiate.

He wonders what kind of job Sammy's thinking of gunning for when he sees the bombshell walk out the front door.

"Sammy, you little shit," Dean breathes. She's got golden curls and legs up to here, and a gorgeous set of hooters encased in, oh God yes, the hottest Nurse Outfit number that Dean's ever seen, with red and pink trim and a skirt that's just long enough to keep her modesty. And a rock on her finger, Dean reminds himself. Hands off. Not even allowed to hit on her. Damn it.

Who's the lucky girl? He'd asked, and he'd practically heard Sam blush.

Jess. Um, Jessica Moore.

Sounds normal, Dean had pronounced, slightly obnoxious about it, but the shock had been giving way to bad humor.

He steps out of the Impala before she passes so he doesn't totally startle her, and casually makes his way onto the sidewalk as she passes by. "Jessica Moore?" he asks, trying to sound unsure and surprised, but he's sure.

She looks up, blinking. "Hello? Have we met?" she asks, not-quite-innocent, a little wary. Dean reflects that sometimes he comes on too strong when he's not in bars, where subtlety isn't exactly called for.

"No, can't say we have," Dean says nonchalantly. Which is hardly fair, and not in the 'damn-she's-hot' way, either. It hurts that he's been out of Sam's life so long that he's gotten a hot girlfriend – fiancée – and Dean never got to know.

He sticks out a hand. "Dean Winchester, Sammy's older brother." He checks to make sure he's not overstepping, seeing the flash of the ring on her left hand. "I hear it's gonna be 'Jessica Winchester' soon."

Jessica blushes a little, and smirks in a way that's not unfamiliar to Dean – a habit, perhaps, that she got from Sam? "So, you're the fabled Dean," she says with a nod, taking his hand even as she walks. "I can't say that I've heard a lot about you, but you look like your picture. Are you looking for Sam?"

"Eventually, but I couldn't pass you up on account of my baby brother, could I?" Dean can't resist saying, giving her an appreciative look. Jessica looks uncomfortable, though, and Dean backs off hastily. "What's the occasion?" He knows full well what day it is, but it's what comes out of his mouth, so he sticks with it.

Jessica gives him an inscrutable look, then shakes her head, chuckling. Sam probably fell for that chuckle, Dean thinks. Dork. "Let me guess: you don't like Halloween either."

Is that what Sammy said about it? Dean wonders, just barely flickers of thought, if Sammy prefers to stay in on Halloween. Salts the doors and windows like they were taught, on this day when the veil is at its thinnest. Does he still have that silver knife Dean gave him? It looked decorative enough to pass it off as some kinda collectors item, Dean had figured. "I can't say I hate what it brings out in the ladies," Dean says, raising his eyes across the approaching campus and seeing other girls in goofy outfits, and guys in zoot suits and Wolfman masks. "Yeah," he continues, brushing over his innuendo – damn, if that gets back to Sam he's going to get the Glare of Death – "Sammy's never been much for Halloween. Where is the little punk, anyway?"

"In class," Jess shrugs, giving Dean a look like she's not sure she should say more, and Dean raises his eyebrows.

"Still?" he blurts. Doesn't that mean it'll be five years in college? Isn't the norm four years? Dean tries to imagine his brother flunking out, because that's the only explanation that readily comes to mind, and he just can't see it. Even when he had to go on a hunt the day before a test, came back bruised and tired at three in the morning, he still aced everything.

"Well, yeah, it's only 10 o'clock," Jessica says with another disbelieving laugh, not understanding the question. "It's a three hour class. Pre-law is pretty tough, but if anyone can do it, it's Sam." Jess says it with confidence and admiration, and Dean decides right then and there that she passes the test: she appreciates Sammy the way he should be appreciated.

Though the apparent major is news. "Pre-law, huh?" Dean says wonderingly. Their pace is slowing, and Dean realizes he's followed Sam's fiancée right up to the front of some fancy-ass building named after some dead guy. "Never would have thought it." Sammy the lawyer. Okay, maybe he can see it.

"Really?" Jess asks, turning to him. "He didn't tell you he was planning on going to law school?"

He never told me he was thinking of giving you that ring either, sister, Dean thinks, feeling bitter and worn down for a moment. Give him a poltergeist any day; dealing with the supernatural is easier than standing here, trying to navigate Sam's mind from a distance, standing in the middle of the cookie-cutter life he's always dreamed of. "Nope. Not sure if you noticed, but Sammy's …" Dean dips his body a little. "Not been that close to his family for a while."

"Oh no, I hadn't noticed at all," Jess says, the sarcasm in her voice belied by a blooming smile. "Sam's class is in Polya Hall, that way." She points. "He'll be out at noon. Why don't you meet him?"

Dean hesitates, only because he can hardly believe he's going to meet his brother face to face, and he's going to have to decide whether or not he wants to deck Sam before asking how he landed Jess. "Sure," he says. "Have a nice class."

He waves her into the building with a fake smile. Or not so fake as he watches her ass.

* * *


It's two agonizing hours, sitting in front of a pansy-ass coffee shop to kill time, sucking down the blackest coffee the pansy-ass shop has to offer. He calls Dad's phone on a whim and a hope – maybe, just maybe he'll pick up.

The number you are trying to reach has been disconnected, says the automated female voice on the other end, and Dean feels his stomach drop into his shoes.

"Fuck," he swears at the phone, drawing startled attention. Dean doesn't care. He snaps his phone shut and presses his forehead against his hand, shaking his head.

He's always done everything his father wanted, everything he thought his father needed, and now, when Dean needs him, he's not there.

Dad is a jerk, he thinks, not for the first time, and he closes his eyes in shame.

At noon he backtracks to Polya Hall. A stream of students emerges five minutes late, half in costumes, and Sam is there, towering above them in jeans and a shirt that looks like it came from one of those preppy mall stores. He can't help towering, Dean thinks, never could, no matter how much he hunches.

He's talking with a couple of guys. Laughing. Fuck, Dean thinks, it's not fair. How long had it been since he's heard Sam laugh? Longer than four years, that's for damn sure. For a moment Dean feels like a relic standing there, a reminder of what Sam always hated, and he's furious.

"Sam," he says.

Sam looks up and meets his eyes. Freezes. Then turns to his friends and says something to them, waving goodbye as they go.

Dean walks forward two steps and Sam closes the rest of the distance. "Dean," he says, and fuck, but there's nothing else to say.

Dean grasps for words. Sam's face is guarded, disbelieving, maybe a little pleased and at the same time uncertain, like he thinks Dean is going to knock him out, shove him into the trunk of the Impala and drive away without looking back.

Not a bad idea, really, but the aftermath isn't something Dean wants to contemplate.

"Met your girlfriend – fiancée," Dean says, to break the tension. But Sam's face goes even more shuttered, and all Dean can think is that he's got to knock Sam out of this. "Fuck, Sammy! How'd you land a bombshell like her? She's way out of your league, man." Yes, obnoxious, it's definitely the way to go.

"It's Sam," Sam says, although there's a flicker of what might be amusement behind the drawn face. "What, I can't marry a hot woman?"

Dean grins. "You're just lucky she met you first," he says. Hesitates. "That nurse outfit …"

"Don't," Sam says suddenly, startling Dean. "It's supposed to be a surprise," he explains. "I get to see it tonight."

"Oooh," Dean says, nodding knowledgably. "Tonight."

"Shut up," Sam says, shoving Dean in the shoulder. "Jerk."

"Bitch," Dean says, with feeling, and it's almost normal.

Sensing the change in tension, Sam turns and starts walking, and Dean follows. "So, college boy, I hear it's pre-law for you."

Sam flickers a smile and ducks his head; it's the look he reserves for girls he has a crush on or academic accomplishment, and Dean tenses. "Yeah," he breathes. "I've got an interview on Monday."

Dean's lost. "An interview for a lawfirm?" he asks, halfway fearing and halfway hoping, for Sammy's sake.

"Hell no," Sam snorts. "Law school. You know, how lawyers get to be lawyers." He says all this like it's obvious, like he can't believe Dean doesn't know the steps into his career of choice.

"Oh, of course," Dean says, purposely mocking. Fuck you, Sam. He's proud of Sam, even if he can't understand, but that doesn't mean he likes it when Sam lords his knowledge over Dean.

Sam ignores him, though. "They're offering me a full ride," he says reverently.

That's no surprise to Dean, but it is a little relieving. Sammy never flunked out; pre-law must just take longer than other majors. The thought of Sam taking more classes stretching out over the years would hurt more if Sam hadn't already declared his allegiance to Ordinary with the ring on Jessica's finger.

"Dude, awesome," Dean answers, because it's the right thing to say.

Sam nods once, then again, more thoughtfully. Dean wonders what his kid brother is thinking, before Sam suddenly turns to him.

Dean senses a chick-flick moment coming, and he wants to run. He can't take this; it's hard enough just nodding and smiling and agreeing that yeah, this is awesome, little bro, I'm so happy that you're getting what you've always wanted, only I'm really not because this isn't anything like what I wanted, and right now I'm feeling like a selfish little shit. But he stays where he is, planting his feet because he's rooted to the spot by the imploring look in Sammy's eyes.

Sammy's about to ask him to do something, and Dean braces himself.

"Dean … would you be my best man?"

Woah, that was kinda out of left field, only not really which just makes it worse that Dean never saw it coming. He's pole-axed for a moment, and he thinks of a million excuses. I dunno where Dad is. Man, I dunno if I'll be free enough for that, you know, the family business. You don't really want me there, do you? I'm a freak, and I'll just remind everyone else how much of a freak you are too. I'm doing the best I can here, man, I'm biting my fucking tongue and playing along, and now you want me to participate too, you bitch!?

Goddammit, those are the puppy-dog eyes. And Dean is not falling for it, not this time. This isn't a bag of M&Ms Sam wants this time; he wants Dean to say yes, Sam, of course, like Dean is really gonna let Sam go just like that. It's obvious Sam hasn't thought this whole thing through.

"Jesus, Sam," Dean says, searching that pathetically hopeful face. "You're really going through with this." And that was the wrong thing to say, but everything was the wrong thing to say just then. Sam's face tightens, and Dean wants to take it back so badly, but not badly enough.

Damn it, Sammy, I owe you this. You owe me this.

"Of course I am," Sam snaps. "You don't buy a girl a ring on a fucking whim."

This is totally the wrong place for this conversation, but Dean doesn't care and Sam doesn't seem to notice. "I know, Sammy," Dean placates, because if he digs too deep with every word, Sam will just stop listening. "It's good – I mean, she's good. Seems like a good person." He barely gets the words to come out right. "But—"

"But what, Dean?" Sam practically spits, and Dean thinks it might be too late to save Sammy's temper from the boiling point. "It's too normal, right? And I can't do normal because I'm a freak?" It's an old insult, one Dean stopped dishing out when Sammy was thirteen and started taking it personally.

Dean's not thinking things through fast enough to beat Sam at a game of words now, though. "Well, yeah," he says before realizing he's going to have to explain that one. "Dude, we're all freaks. We're a freaking family of freaks!"

Sam's jaw twitches. Dean rallies himself, and throws out the sixty-four million dollar question. "Does Jess know what you do?"

"Did," Sam snaps.

"What we do," Dean presses, twitching a finger between himself and Sam to indicate the whole immediate Winchester family. "Does Jess know?"

Sam is silent for a long moment, which is answer enough. Dean feels smug and sick at once, betrayed, but his point proven. "Thought so."

"It doesn't matter," Sam says tightly. "She doesn't have to know."

"Yeah?" Dean shoots back. He glances up and down the sidewalk; no one in listening distance as long as they don't start a shouting match. He grabs Sam's elbow and guides him, walking his taller brother towards a quieter, grassier place. Sam lets him, which would be a surprise if he hadn't just revealed that his whole past was a big honking secret. "You know what's out there in the dark," Dean mutters harshly as they walk. "You can't just ignore it. You're not going to keep silver bullets around? Iron shot and rock salt, just in case? Dude, even if you're not hunting, you're never going to be able to just walk away forever."

Sam yanks his elbow free of Dean's hand. "Yeah?" he echoes harshly. "Watch me."

And he turns and walks away.

* * *


If Dean were his father, he would just let Sam keep walking. Probably would stomp off in a huff himself. But Dean is not his father; his father is at the other end of a disconnected number, and Dean can't stand it. His whole family is running away from him, as fast as they can in opposite directions, and it's scaring Dean to death.

"Sam," he implores, walking after him, stretching his strides longer to match Sam's. "Sammy, for fuck's sake, what are you, five? Gonna walk away in a temper tantrum and pout all day?"

Sam's jaw twitches again. "Maybe," he says, voice dark.

"Always so melodramatic," Dean grumbles, loud enough for Sam to hear. "Freaking drama queen."

"Go away, Dean," Sam says, not looking back.

"No," Dean says. "God, Sam, I'm saying this for your sake. Think it's healthy to go off and marry a girl when she doesn't know half of who you are?"

And for some reason, that grabs Sam's attention. Sends him whirling on Dean, grabbing him by the shoulders of his leather jacket. "And what am I, Dean!?" he demands, really angry now. "What do you think I am!?"

My little brother, too smart for your own good, too clever by half, stubborn, independent, obnoxious, whiny, bitchy. And my responsibility. "You're lying to yourself and your girl," Dean says instead. "God … you're too smart for that. Hell, Jess is too smart for that, if she's smart enough for you, Brainiac."

"You don't know anything about it," Sam breathes, but he falters at the backhanded compliment. He releases Dean's shoulders. "What the hell am I supposed to say to her?" Sam asks, and it's a genuine question, from younger to older sibling. "She'll think I'm nuts."

"Maybe," Dean allows, and hates that part of him leaps at the suggestion, hopes Jess will run for the hills and break Sammy's heart and teach him once and for all that normal isn't always peaches and sunshine. "But maybe not. Sam, if she loves you enough to take that ring, she'd damn well better be able to take the truth about you, too." He claps a hand against Sam's shoulder. "Like it or not, hunting's a part of you."

"I'm never going hunting again, Dean," Sam says seriously, meeting Dean's eyes.

Dean looks away.

"Yeah, got that message loud and clear two years ago," he says, and feels Sam flinch from guilt. Dean immediately withdraws the knife. "Seriously, though, you lived our gig for eighteen years, man. You can't pretend that away."

"I've done pretty well until now," Sam mutters.

"Yeah, and now you done gone and get yourself a wife," Dean twangs, lifting his eyes again. "You either live with that lie between you all your life, or you get it out there now, before you fuck up someone else's life. Like hers. Or your kids'." It's hard to even say it, to affirm the thought of Sam having kids and a wife. To let it hang in the air between them. But Dean knows it's a low blow all the same, a punch in the gut to someone like Sam, who's probably sworn up and down that he will never, ever fuck up his children the way John Winchester fucked up his.

Dean's glad Dad isn't here now, because he thinks he might actually be getting through, so help him.

"Tell you what, Sammy," Dean says, and continues over the 'it's Sam' protest that escapes Sammy's lips. "I'll be your best man, if you tell Jess the truth." Because if she still wants to marry you, god help me, I'd be a fuckup if I kept fighting back. Dean thinks of Cassie and squashes the memory just as fast. He shouldn't be wishing that on Sam, but he is.

Sam rubs a hand over his face and eyes him. "Jesus, Dean," he swears.

"I mean it," Dean threatens. "Not gonna be the best man at a wedding that's doomed to failure."

There's silence, and Dean can see him debating everything behind his eyes, weighing his options. And it hurts, because Dean knows that Sam could very well flip him the bird and find someone else. Maybe one of those guys he was laughing with earlier.

"All right," Sam finally says, like the words are dragged from him.

All Dean can manage is a little nod.

* * *

A wise man once said if you love something, let it go. If it comes back to you, it is truly yours.

Dean thinks that's shit as he guns the engine, ready to head up to Jericho in search of John Winchester, who phone has been disconnected for days now.

He's let both his father and brother go, and they're never coming back, never even glancing towards what's behind them. But Dean knows they are his, just the same.

All he can do is cling to what he's got.


A/N: And then, three days later, John rescues Jess from the demon because despite Dean's belief he's been abandoned, John totally got his message about being in Palo Alto before his phone got disconnected because he didn't pay the bill. Sam lives happily ever after, and Dean and Sam get the Colt and kill the YED together, then go live in Palo Alto and make goo-goo faces at their grandkids/nephews/nieces. This ending is pasted on yey!