Ik realistically Dean was probably in the closet for a loooonnnnggggg time BUT!! It’d be freaking hilarious if not!
And by that I mean:
When Sam when to Stanford and John started leaving Dean alone for longer periods of time Dean was like “wait this is my perfect opportunity >:)” without John breathing down his neck he went on a sexuality journey. And because he’s Dean Winchester obviously it was either go big or go home. So he went big.
And that’s how the Cartwright Twins happened.
And ever since then he hasn’t outright told anyone he was bi but he doesn’t keep it a secret and it’s kinda super obvious
Except it would be super funny if Sam just didn’t realize and tried to have a conversation with him about it..
And Dean goes “bro I’ve been screwing dudes since I was like 22”
And ofc Sam is like wtf and so Dean clarifies and that’s how Sam finds out he had a fling with just about every man they’ve ever hunted with.
(Sam almost loses his mind when he founds out about Benny…)
And also that he’s marrying Cas in September.
(Sam almost passes out at that)
(He actually does end up passing out when Dean lets his… party… with the Cartwright Twins slip)















