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Dean stops.
Stops drinking. Stops sleeping with random women. Stops going to the bar altogether. He stops eating burgers because hey, meat was an animal, and it's wrong to kill something breathing, right? And monsters? They're breathing. So he stops killing them too.
Dean stops lying to Sam. And he stops idolizing Zeppelin. He stops rolling his eyes at Christian rock and he stops the maybe-too-much pride he exhibits when, for once, he knows more than his little brother about that one random historical fact.
He stops stealing credit cards and telling people he's FBI. He stops hitting 'replay' after the tenth time watching his favorite Busty Asian Beauty crawl into bed with the mailman. Hell, he stops watching porn altogether. Dean stops swearing, doesn’t let a single S.O.B. out of his mouth. Yes, he stops saying "Son of a -----!”
Dean stops a lot of things.
Mostly, he stops lying to himself.
He starts admitting that he likes the way Men of Letters shoes are a little less manly and a little sleeker and a little more stylish. He starts finding new ways to add flavor to salads and he starts trading smirks for neighborly smiles, turning away if the waitress still takes his hearty tip as something more. He starts spending his free time as a volunteer fireman, and eventually he starts working for them too. He starts earning an honest living like an honest man.
When he finds out that the local church hosts meals for the homeless every Thursday, Dean starts dropping off pies. (He does his best to ignore blue eyes, a blue vest, and a rolled up sleeping bag that come with the sight of the Gas N Sip across the street.)
One day, on his usual pie drop-off, a surprise storm outside the church entices him to stay and he start serving the food too, even bows his head when they pray.
Dean starts attending Sunday Worship and Tuesday AA meetings because old habits die hard and he's no longer too filled with pride to admit that.
He starts praying too.
He starts apologizing for every time he's ever fallen to the seven deadly sins and he starts spilling his many, many wrongs in the confessional booth (much to the horror of the priest).
After his sixth or seventh trip to the confessional booth, he starts telling Sam the truth about why he won't eat at their favorite diner anymore, but he's cut off by his own sobs while he explains that he doesn't want to risk hearing the flap of a tablecloth being changed because last time, he looked over his shoulder and expected to see--to see--
He’s quiet for a week after that.
Dean starts calling Jody more often and eventually asks if Claire happens to be on college break and does she wanna help him keep track of the church's youth group tweens? They’re going to the new put-put place in Lawrence and could use another chaperone. Or at least someone that can indulge their juvenile Happy Gilmore references.
He starts living a civilian life - near apple pie life, in fact. Because as much as any one human can, he stopped sinning and started living a life worthy enough to maybe, just maybe, be invited into those pearly gates he used to scoff at.
But he knows he won't make it.
Because the one sin he couldn't stop was envy.
He couldn't stop his hand from crumpling the edge of the letter from Jesse and Cesar, even though they just wrote to extend their condolences.
He couldn't stop the silence from going on too long when one of the church youths confided in him that he liked a boy in his class, nor could he stop his own mind from screaming too little, too late. He could hardly stop his mouth from spitting out a selfish “at least you have time.”
He couldn't stop himself from breaking his phone against the wall when Claire relays what an angel told her. About Amelia and Jimmy's reunion in heaven.
Because no matter how true and holy he tries to live, there's this endless nagging feeling that he'll never be able to clean his soul enough. That his best friend will be forever alone and waiting in their heaven while Dean just gets dragged right back to hell where he belongs.
As he gets older - as his knees begin to lock and his hair begins to gray - Dean stops dreaming. But he starts having nightmares that remind him of Billie’s promise -- that mock him about The Empty and the space there reserved for a Winchester. Any Winchester.
Dean starts waking up in a sweet because even if he was lucky enough to get into heaven when his clock runs out, his door might have two names on it.
But he might be the only one there.