I absolutely love it when, in fanfics, Dean is absolutely shocked that Sam knew of his bisexuality. It's like my favourite part of any destiel fic.
But every time I watch Supernatural, I see a (mostly unspoken) understanding between the brothers.
Like Dean will shamelessly flirt with or check out men around Sam, and Sam never bats an eye.
When Sam called Dean out on how him being "butch" might make people think he's overcompensating, Dean just said "right" all awkwardly.
When Dean spoke of his relationship with Benny to Sam, he used the word "relationship" without worrying about the implications of it (even if they weren't actually in a relationship)
When Dean told Sam that Aaron was his "gay thing," Sam moved on from it almost instantly, and Dean never felt the need to explain it away.
When Dean was flirting with that male cop, Sam had to pull him away, and Sam's only expression was annoyed.
Before Sam knew sirens could sire people without sex, he didn't react when Dean's siren was a man.
When Dean meets his celebrity crushes, he gets all flustered, and Sam is never bothered (confused, shocked, etc)
Dean will make queer references
Sam will make little comments ("...or are you strictly into Dick now?", "I forgot about you and Crowley's summer of love", etc)
I don't think either of them are unaware of the other's knowledge.
They both know, and they both know that the other knows.
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