New York City is known for being packed, but the coincidence that Sam and Dean Winchester would live in the same apartment complex as two Novak’s and one Charlie Bradbury is pretty crazy. They didn’t even know each other, how much of an impact they could be on each other’s lives. Well, Dean knew Charlie Bradbury, the tenant three doors down, but he knew her because she had gone around a month ago asking people if they wanted to go to her Doctor Who 50th Anniversary party and of course Dean said yes, Matt Smith and David Tennant breathing the same air? Oh yeah, he was totally going to become best friends with her. And he did, even before the party they talked about everything and everyone.
It wasn’t long until he introduced his little brother, Sammy, to Charlie and those two became book nerds together. What Dean didn’t know was that Sam was good friends with Gabriel Novak, a man one floor down and two rooms away. Gabriel, as Sam knows, is a little bit of a trickster and loves a playful challenge. So when Sam gets into the elevator one day and meets a blue-eyed man by the name of Castiel Sam goes directly to Gabriel and asks him about Castiel only to find out it’s his little brother.
Hearing this Sam asks more and more about Castiel and the more he learns the more he starts to smile. Gabriel asks Sam if he’s ‘into’ Castiel and Sam laughs, “No but I think my brother would be.”
That’s how it started, it’s all Sam’s fault for placing the thought in Gabriel’s head. Gabriel, the eyes and ears of the building knew everyone and everything about that building, and in all honesty he couldn’t agree more. So that’s how he hatched the plan, and put a package with Castiel’s address in front of Dean’s door.
That’s how Dean first met Castiel, via that package. It was his first day off in awhile and he planned on sitting around his apartment watching LOTR the director’s cut when the door bell rang and he had this mysterious package in front of his door. Figuring he might as well drop it off at the real tenant he went up to the apartment and knocked on the door.
He had never, ever, seen a man more beautiful than Castiel. The man apparently just woke up and looked sleepy as hell but smiled like it was the sun when Dean explained what happened. Some way or another Castiel ended up at his apartment, watching Lord of the Rings with him (because Dean wasn’t going to let someone so attractive get away with not knowing about Lord of the Rings).
They soon became close, closer than Dean was with Charlie, and as close as Dean was with Sam, just in a different way… really different. Dean fell asleep thinking about dark pools of cerulean and soft hands and rough stubble. It was becoming a problem.
Soon enough all five tenants got to talking, Gabriel with Sam and Cas, Dean with Charlie and Sam and they planned a large get together at a locale cafe/bar. To this day that evening would go down as one of the best times in Dean’s life. It was the day that he and Cas first kissed, the first time they held hands and it was perfect.
Over the next couple days the two boys were inseparable, Dean’s days went: Sleep, Work, Cas, Food, Cas, Cuddles, Sleep, Repeat. Soon enough Cas didn’t even live in his own apartment, allowing his lease to expire and for him to move in with Dean. That was probably the best moment in Dean’s life.
Well that and a couple years later when they moved into a small house outside of New York City and got married. But that, that’s for another day.