I think you hit the nail on the head with 'gender non-conforming.' I think Dean feels compelled by the way John raised him to perform gender in a way that isn't authentic to him; that while there are so many different ways to be a man, he has been forced into the one that fits him badly. I don't read him as trans or woman-coded or whatever (and yeah, 'woman-coded' is so often just a slide into straight-up misogyny), I read him as being a man who is not 'stereotypically masculine,' but knows how to wear that mask.
Because, you know, men can like sexy pink satin, cook, care for people, be intuitive and emotional, admire and relate to women, and desire men. All those things are things a man can definitely do. And Dean does. I think he would love to not comply with gender, but he doesn't have time for himself in that way. He's too busy being god's favourite toy.
aww thanks! of course i agree about john's expectations of dean's behavior when raising him. but i think that's complicated by john both wanting dean to act in ways that are stereotypically masculine (teaching him how to use a gun at a very young age (1.18, 2.06, 11.08) and also saying things like, "that's my man" to an elementary schooler (1.18). but he also expected dean to do very stereotypically feminine things: frequent primary responsibility for feeding and caring for a child (i literally cannot cite all the examples of this godbless that is the whole show (to meeee)).
and i think that from what we've seen of dean's personality, the second is the one that comes much more naturally. he LOVES to cook and feed his family (and anyone). and while i definitely don't like the forced parentification or repeated forced responsibility dean experiences over the course of the show, i genuinely do think if given the choice, he would chose to care for and cook for and clean for his family in ways which are extremely stereotypically feminine.
and i think the way that that came naturally to dean and the amount of laundry, cooking, dishes, and sam's school-prep he did as a child probably made john lean a little harder on all the ways he wanted dean to still "be a man" etc. it can't have been easy for john, who already felt he was semi asking his kids to pause their lives so he could do his Hunt, to see dean to some extent pausing his growth into manhood by having to fulfill these feminine roles. i mean in 14.13, john emphasizes the normative hopes and expectations he had for dean. of course john wanted him to listen to rock music and was pleased when it seemed like dean was starting to sleep around.*
and of course dean learned to put on that mask.
i think it really is beautiful as the show goes on to see him let the mask go more and more. from little things like cooking lots in the bunker and wearing his special apron to his comfy purple pajamas - and in general more whimsical home clothes (noodle socks, scooby-do boxers, hot-dog pajama pants). to feeling he can express fear and discomfort with more ease ("always am" [scared] (15.16), not wanting to go in the tunnel (13.06), spiders (13.08), "never said i wasn't scared" (14.12), "hot bread" (15.20**). to his self confidence ("i'm good with who i am" (14.13), "lady, i'm tolstoy" (15.11), talking about retirement (13.23)) beyond his assigned role as value through self-sacrifice alone.
all of those signs lead me to believe that as time passes, as his life is less fraught with danger and conflict and death around every corner, he will have the time and space to heal and to bloom into more of the person he wants to be. and all signs point to that person being very different from the person that john, chuck, alastair, amara, gabriel, michael(s), zachariah, cain, crowley, even sam, and certainly anyone who values rigidly defined gender differences would expect.
(also your line about dean admiring and relating to women is SO spot on. i just have to shout that out. i just watched 2.18 and the way he is so impressed by tara's acting (speaking of acting and masks etc!!) is so charming to me. i said more about how dean sees and respects women's performances here. but yeah i loved how you said that!!)
*okay that one is from john's journal im sorry. but it tracks for me.
** this one makes me genuinely ill
