Okay, this is what I wrote over vacation. I expect we'll return to your regularly scheduled crackfic programming shortly.
Title: From The Start (It Fell Apart)
Genre: Gen, though there are overtones, depending on your inclinations
Rating: PG-13
Spoilers: Through S4 (though nothing too specific)
Warnings: None that I can think of
Summary: The first time Dean ever fancied himself in love, he was just old enough to be completely stupid about it.
**
The first time Dean ever fancied himself in love, he was just old enough to be completely stupid about it. She was some fancy rich girl, pretty and spoiled and she had Dean pegged the moment he rolled into town. They were hot and heavy from day one, which Dean chalked up to his natural charm and charisma.
Until he overheard her arguing with her mom. It was quite the cliché, really. Started out with, "You don't know him!"
"Oh, I know Dean," her mom said. "I've known a ton of Deans. Boys like that are a dime a dozen. He is common. You can do better and you know it."
The argument had ended with, "I hate you!" When she slid into the Impala, she didn't look distressed or upset. She'd looked excited.
Dean knew the score, then, because he actually wasn't stupid. He knew that she was there because she thought he was beneath her. Some good looking piece of trash that she could use to piss her parents off with. Because if nothing else, he was attractive enough for her to deign to slum it with.
He says he doesn't remember her name, years later when he's telling Sam the story as a warning. Sam says, "So did you break it off, then?"
"Naw, man." Dean grins without humor. "I fucked her until we moved." Whatever else that chick took away from the experience, she'll always remember how much she wanted him. Dean made sure she wouldn't be able to lie to herself about that.
Sam gives him a look, one that is way too old and knowing. It's really fucking obnoxious. "You shouldn't let people treat you like that, Dean. You're not-You're better than that."
"Yeah, well. We know that, right?" Because, really, that's what matters.
"I do," Sam says.
Dean chooses not to dignify that and the conversation ends there.
***
The second girl Dean fell for in any serious way was, well, awesome. She was adventurous and dirty as hell and Dean seriously considered marrying her. Well, fantasized about it at any rate. There was a long stretch of time where he might have followed her to hell and back. Until the day he came home to find her fucking his baby brother.
Sam was fifteen at the time.
He waited until they were done, then told her to get the hell out. It wasn't even the fact that she wanted to sleep with them both. Hell, as they got older, it happened from time to time and they had more than one bonding moment of, "So, hey. How did you like that thing she did..."
It wasn't even the fact that Dean was a little bit in love with her, because there's nothing he wouldn't share with Sam. Which registered pretty high on the fucked-up meter, admittedly, but it was true nonetheless.
The problem was that, as far as Dean knew, it was Sam's first time. And the guilt and self-loathing on his face for snaking Dean's girl is something Dean will never forget. If she had even come to Dean first, they could've worked something out. He could have let Sam know that it was alright.
Even though afterwards Dean reassured him, he knew that Sam would always feel a little bit guilty about it and that's the part that pisses Dean off. Still. He can't ever forgive her for fucking up Sam's first time.
Her name was Chastity. Dean's pretty sure she became a stripper.
***
The third girl was after Sam left and Dean was so goddamn alone he started to feel like a ghost himself. Dad was around, of course. But John Winchester had always belonged to his dead wife and Dean-- Dean had always belonged to Sam and Sam was gone.
And Cassie was so normal and great. Funny and smart and she seemed to think Dean was worthwhile. It was nice, easy in a way that seemed almost functional and Dean was so fucking needy that he went and told her everything. Everything about the family, what they did, about the ghosts and monsters and waking nightmares. He dumped it all on her at a point in the relationship where most people would be revealing their aversion to musicals or movies with Nicholas Cage in them.
Because god he needed someone to know him. Needed it so badly that he never stopped to think how it might sound. How someone might react, that it was something that other people needed to process. He hadn't given her time for that and she got the fuck out as quick as she could.
She was the first girl who came close to breaking his heart. She might have, had it not already been broken.
The second time they part it's on amiable terms and Dean isn't quite able to recall the thing he felt for her that was so devastating at the time. She's a nice girl, was all he thought as he and Sam drive away.
He hopes things have worked out for her.
***
The fourth girl is sort of a delayed reaction. Dean's dream girl after the fact. She was, in reality, a fun weekend. It was more what she represented, with her kid who could have been Dean's. In another life. The life Dean didn't get to have.
Lisa was always a fantasy and Dean knew this. He never had any illusions about making things with her work. Because Dean fell in love with her when he had a set expiration date. She was there only to illustrate what he could never have in an acutely painful way that he could understand.
Or maybe she was there to let him know what other people got to have because of the things he did. That he mattered, made a difference. Life wasn't fair, but it balanced out in a larger cosmic way.
Which, as it turns out, is bullshit, but it was a nice thought.
***
Dean tries to stick with girls who know the score, who are playing the same game he is. Everybody has their fun and goes home happy. He treads lightly around the girls who deserve better than the likes of him and tries not to catch himself in their snares. It doesn't always work, but he still does what he can.
He knows, has known from an early age that the fluid, transient nature of his life prevents him from having the relationships other people take for granted. There are times when he feels more like the things he hunts than those he protects. He slides in and out of people's lives, they slide in and out of his. Only there in the moment and then it is gone, he is gone. Fading, burning, blurring, memories tucked away in those places to be forgotten as soon as possible. So often they want to forget the thing that's brought Dean to town.
There are so many things Dean wants to forget.
So he tucks them away, too. All of those moments where people have skimmed to touch beneath the surface he projects. Those sparks and connections that keep Dean grounded in the world. They are fleeting illusions, things he can't have. They waver and dissipate like reflections on water if he tries to reach out and touch them. These have never been the things that keep Dean grounded. Not really. Even though they should be.
Which isn't to say that Dean's never been in love, but that's a different story entirely.