Don't you dare think that there is anything, past or present, that I would put in front of you. It has never been like that, ever! I need you to see that. I'm begging you.
Dean has a box full of postcards and letters he wrote for Sam when he was in Stanford
[Stanford era] Sam prayed for Dean to be safe every night [Bonus: Sam still does pray every night]
Sam’s first kiss: 4th of July 1996 (guess who he had it with) (Dean) (duh)
Dean doesn’t have a specific moment of when he fell in love with Sam– he’s always been in love with him. It just took him a while to realize it.
Sam gets off to being called ‘baby brother’ in bed :)))))
Dean called Sam’s cell from time to time, but the moment Jess answered his cell, he never found the courage to call again.
Sam loves school but he loves Dean more. The reason why he left for Stanford was because he needed to put space between him and his brother.
Sometimes Sam tricks Dean into eating something healthy. Dean hates it.
They once flooded the motel bathroom because they wanted to take a bath together. It was hilarious. It started off as romantic but ended up with them having a water fight.
Dean’s a sentimental fuck: he keeps all of Sam’s childhood things in a rented lock box back in Kansas.
Sam’s purple dog shirt? Dean bought it for him as a joke.
All of Dean’s hookups have the same qualities: petit with long brown hair and hazel eyes.
Sam never cuts his hair because he likes the feeling of it being pulled when Dean fucks him.
Dean playfully calls Sam his wife. It started when they were kids and ended after Sam left for Stanford. It was brought back to life when they moved into the bunker.
In every universe (like the It’s A Terrible Life!verse, and every other parallel world beyond their own), they always manage to find each other and fall in love. How? They’re soulmates. Simple as that.
I have soo many headcanons tbh but i’ll stop here (◕‿◕✿)