Rated M for Language.
Dean was the sort of person who was filled with endless regrets, like the sort of memories that were never wanted but always remembered, and the things that gnawed relentlessly at his gut until he couldn't stand it anymore, and let alcohol wash them away. He'd spend hours in the car while Sam slept, mulling things over, trying to discern if he'd actually done anything right in his entire excuse for a life, and for all the time spent brainstorming, he could only ever think of four. Four things that he'd done in his life that were worth it, that he'd never take back even if he could, even if he wanted to, even if.
The first was running out of their house with his baby brother clutched tight to his chest all those years ago.
Images from that night still flashed through his mind, a staccato tempo of fire and smoke, choking on tainted air and his fathers screaming. He still woke in cold sweats, panicked something fierce until he'd located his brother's sleeping form, heart calming behind battered ribs. He could still hear Sam's crying, wailing sobs that scared him more than the fire, more than the cops and the paramedics and the fact that his mother never joined them outside. He'd been too young to understand it then, but he caught on pretty quick, how fire was dangerous and their mom wasn't ever coming back. This wasn't like the times that she'd run to the store to pick up bread or milk, no, this was different, this was permanent.
No matter how much he wanted to have his mother back, to have her come running from the house after them and pluck Sam from John's arms, cradling the three of them close… he wouldn't change it. Ignoring how insane he sounded for saying it, Dean wouldn't stop the fire, even if he could.
Anyways, growing up without a mother taught him how to be a big brother.
He learned what sharing meant far better than other children his age, always sharing a motel bed or his sandwiches or his toys. He discovered that taking care of someone other than yourself can be rewarding, and that family is undoubtedly the most important thing. And, it may have taken years for him to fully grasp the concept, but eventually, he even understood that, sometimes, you have to make sacrifices to protect the ones you love.
That's why he'd never be able to bring himself to regret making that crossroads deal, his life for Sam's, no matter how many times he died.
He'd go to hell and back for that kid a thousand times over, easy. Even if he'd jump started the apocalypse, even if he was falling apart at the seams and dying from the inside out, he'd do it again in a heartbeat. Sam was… well, Sam. He was his baby brother, his best friend. Maybe selfishness had been the driving force behind his actions. Maybe it was the fact that there was no way ever that he'd be able to live without him, maybe, but he couldn't regret offering up his soul.
If there ever was a worthy cause, Sam was it.
The third thing he'd never regret was declining the invite to be an angel condom.
He couldn't even begin to fathom saying yes to Michael, and letting that jackass of a celestial being parade around in his body, destruction of the earth imminent or not.
There was a damn good reason that he'd been born who he was, and even if practically everybody and their father seemed to be telling him that he'd been born to be the vessel, screw them to hell and back again. Honestly, even if he had to go through that whole thing again and again and again like some horror movie stuck on replay, he'd still say no. He was Dean motherfuckin' Winchester, protector of good, vanquisher of evil and dick angels galore.
And then, there was the fourth thing that he could never, ever, ever bring himself to regret - kissing Castiel.
It had been nothing more than a spur of the moment decision, where he'd just grabbed the angel by his lapels, bunching trench coat in his fists, and thrust him into the wall, mouth savagely attacking his lips in a manner that scared the bajeezus out of Dean. He'd kept his cool despite how his blood was racing through his veins when they parted, breath coming in short pants, but he'd lost it at the look on Cas's face - bug eyed, lips parted and red, exactly like a doe caught in headlights - and he doubled over in laughter, simply because that was the most expressive he could remember the angel being, ever, and it made him happy to see.
That kiss was probably one of the best he'd ever had. It was worth Cas not showing up for weeks, it was worth him staying at least three feet away any time he did pop in, it was worth the awkward silence and extreme discomfort radiating from the angel for the next several months. It was worth every clipped sentence, every hesitant touch, everything that happened, and more. And he'd do it again in a heartbeat.
So, even if the world would've been better off without some of the things he'd done, or some of the choices he'd made, he wouldn't alter the path he'd taken in any way. Someone had once told him that it was okay to look out for himself once in a while, and that was precisely what he was doing.
The way he viewed it was simple: if he hadn't pulled Sam from that fire, he wouldn't have made that crossroads deal.
If he hadn't made that crossroads deal, he wouldn't have gotten himself a one-way ticket to hell, and he wouldn't have broken the first seal.
If he hadn't broken the first seal, there would've been no need for Castiel to pull him from hell, no need for the angels to interfere in any way, no need for Michael to seek his 'one true vessel'. Dean's idea of faithwould remain forever tarnished.
If angels hadn't been needed, he never would have met Cas, never would've touched him, nor kissed him, or known him. He'd still be rotting in hell, and the world would keep on spinnin', like always.
If his father had broken in hell instead of him, and the angels did come, if they did need Dean, saying yes to Michael would have scorched the earth, and destroyed at least half of the things that Dean was trying to protect. Even if braving the apocalypse was hard, the thought of letting himself be used was far worse.
Without those four things, he would never have made it here, a dingy little motel in some Minnesota backwoods, downing beers by the six pack and laughing over the stupidest things.
He definitely wouldn't be sitting in the middle of the bed he'd claimed (the one without the mysterious stain on the pillowcase), kegs crossed beneath his thighs as he chugged, and chugged and chugged and chugged out of his beer bottle, head lolling back onto Castiel's shoulder.
The angel wouldn't be holding his hand under the blanket, thumb stroking somewhat stiffly over the rough skin of his palm, soothing and warm and pleasant. Sam wouldn't be laying on the carpeted floor with his feet propped on the bed, recounting a memory from way back when in which Dean had worked his ass off to provide them with a Christmas. He wouldn't be with either of them the way he was now - happy - and he couldn't deal with that thought.
After all, this was the closest a hunter could ever come to happiness, Dean was sure of it.