Dean and Sam are raised in a nice house by Benny. They're well loved, though have trauma from when John comes around or the one time he kidnapped Dean, but day-to-day living with Benny is okay. Dean's 18, a senior in highschool. He works at the local diner as a waitor. He loves it, and gets free food. He plays baseball and is sort of a nerd, loving star wars and star trek and loves comic books. He's popular.
Castiel was kicked out of the house at 16 when his parents found his stash of Anne Rice book and Brokeback Mountain on DVD. He's about to turn 19, about to finish his freshman year of online college which he does at the local library, in line with getting a degree in business administration. He's got piercings and tattoos, he wears makeup and clothes that are so tattered and old but somehow makes them look so fashionable.
Castiel meets a girl at the library, Charlie, who invites him to come get dinner with her at her fav diner down the street. He goes, mostly because he wants to keep talking to her about medieval history, but also he'd never been to that diner.
She yells and waves when the walk in, at her pal who works there he'd explained. Cas sits down at their booth in the corner, looking out the window at the cars passing by. Their waitor shows up in his red shirt and jeans that hug his hips just right and that dumb black apron and oh...
"This is Castiel! He works at the library. He likes Star Trek too!" Charlie said as they started at each other, blue eyes glued to green.
Castiel started going to that diner every day. Dean got a library card.
