oh man it really depends on my mood for when i think it finally became a thing. sometimes i think dean and sam knew from a young age (13/17) but didn’t act on it for a few more years. sometimes i think it was hinted at but didn’t come to fruition until after jess died. sometimes i think it happened first for sam and then dean followed suit, and sometimes vice versa.
my favorite spin on it, though, is that it was building up and freaking them out for a while but they didn’t act on it until the night of sam’s high school graduation. dean’s grin all pride, john not rising to the bait if sam even hinted at wanting to argue, and sam just kind of floating in the glow of it all. john bought a bottle to celebrate and they were actually having a decent time until john says, “your mother would be so proud” and then his eyes get a little misty and he excuses himself, goes to walk it off and think and maybe shoot a few bottles off the top of a fence.
dean and sam share the remainder of the bottle, trying to drown away the comment and the melancholy it brought. their fingers would linger a little longer if they touched and they both blamed it on the alcohol. dean nudges sam and says he’s proud of him, “really fucking proud, sammy, so proud” and sam all but explodes he’s smiling so stupidly hard and his head is on dean’s shoulder and dean turns to smile down at him and they both lean in and kiss and it’s everything. the bottle falls onto the floor and glugs and glugs all over the shitty carpet but neither of them care. dean’s mumbling about giving sam a graduation gift, “my body, take it, my gift to you, sammy, always yours, so proud”
in the morning they play it off as a fluke even though dean’s eyes are a little softer on sam and sam is horrified, not by their act but by what it means, what he acknowledged for real: he’s in love with his big brother
that’d be the night he decides he’s going to stanford, can’t put dean through this, though whether he means the relationship or dealing with sam on a whole new level, doesn’t seem right
of course he doesn’t tell them until much later, when the dorm is ready and when he and john have an explosive fight, but, still
~~