I laugh so hard when people say that Dean is 100% straight
even though in canon (multiple times!) he has checked out men, including one time where he stared at a guy’s dick with an appreciative expression for like 20 full seconds.
He has a crush on a male tv star in canon.
He agrees when somebody says that Sam is the “Bonnie to (his) Clyde” and compares himself and another male character to Thelma and Louise.
He has extreme sexual tension with a male character (possibly more than one but that is arguable) which could possibly be argued but everybody knows it’s there.
When he becomes suicidal in season 5 he openly flirts with said male character in canon.
His siren (kay let’s think about sirens for a sec. They show up as a perfect lover and are different for each man, but they usually show up as really hot chicks. Keep that in mind) was a male FBI agent who was a perfected version of Sam. Sirens are, remember, IDEAL LOVERS. Dean’s ideal lover is basically a cooler-but-still-very-male-version of his little brother. The siren even outright states, “I gave him what he wanted. And it wasn’t some bitch in a g-string. It was you.” AND stated that Dean was in love with him. -le awkward-
So at one point Dean was IN LOVE with a male character, he has a crush on a male celebrity, he checks out men, and he has what can easily be seen as sexual tension with possibly more than one male character. Also, he likes wearing women’s underwear, but that may or may not be relevant.
“BUT DEAN HAS SEX WITH THE WOMENZZ!!1!” you say.
Dean also has tried his entire life to be absolutely perfect. He has an image of the ideal man in his head and he wants to be that person. I highly doubt his idea of the perfect macho manly man is gay/bi. Obviously, he wouldn’t just admit that he likes dudes and probably wouldn’t act on any urges/fantasies/whatever either. He’d see it as a failure. Think of how many times he has felt the need to state, “hey I’m hetero.” He talks constantly (although not so much in the current season, understandably) about his sex life, the fact that he likes chicks, he’s always flirting with women, teasing Sam because he doesn’t get laid as much (even though I’m pretty sure sam does have just as much sex as Dean does, if not more).
He makes comments about Sam being “gay” because he’s not the perfect “macho man”. Dean is insecure about his own flaws and feels the need to project them onto his brother. Sam seems like the more “girly” one sometimes because he s generally soft-spoken and more sympathetic towards the victims they have to talk to, or family members of the victims. He’s more reserved, doesn’t drink as much, doesn’t constantly talk about sex. But Sam is the one who’s secure in his masculinity. Sam never feels the need to prove himself. He’s comfortable with who he is (well, not the demon-blood apocalypse-starter stuff, but other stuff) in ways Dean isn’t. And Sam, in reality, is the “manly-er” one. Physically he’s stronger, faster, taller and more masculine looking than Dean. He’s also more violent and he has anger issues. He rarely shows possibly bisexual tendencies like Dean does. Sam is a lot closer to Dean’s idea of the perfect guy than Dean himself is.
I think that perfect guy, in Dean’s head, is John. Dean teased Sam and talked about how much he liked chicks a lot more when his father was alive/shortly after he died. John was tough, he drank, and from what we know he was completely heterosexual. He was probably a bit homophobic (or maybe Dean assumed he was homophobic) because of the whole tough manly man thing. He fought in a war, he was a great fighter, he drank, he wasn’t “soft” and rarely showed emotion. He was the stereotypical macho man. That stereotype does not include liking guys. It stresses that men like WOMEN, have a lot of sex with WOMEN, and Dean sees that as the norm that he has to conform to in order to be what his father wanted him to be, or to be his father, his idol.
Basically, Dean wants to be a perfect manly guy like he thinks his dad would have wanted, and being bi would go against that. He’s insecure because he doesn’t fit into that box. He clearly shows bisexual tendencies in the show and he tries to make up for it by flaunting his sex life and teasing others for not fitting into that box.
I have no doubt Dean likes the ladies. But I also have no doubt that he likes dudes too.
