Okay I was going to put all of this in the tags but it was like. Way too many tags.
First things first, only watched s1-8 so far, and I think Dean is bi (far out and unpopular opinion, I'm aware)
I think that Dean was not intentionally written as bi/gay for at least the first like 4 ish seasons, and if he was it was only for as long as the ‘haha wouldn't it be funny if our super-cool-macho-protagonist was GAY' joke lasted, and once the bit was over he would go back to being straight.
I think the writers' intention with Dean's slut-tendencies (affectionate) was 50% appealing to their assumed straight, male audience, and 50% reflective of Dean's inability to form long-term relationships outside of his family.
I would say S5 (especially following, I would assume, the popularity of Destiel) is maybe when at least some of the writers start to toy with the possibility of Dean being bi a bit more seriously with Dean getting flustered around Dr. Sexy and later on Aaron Bass (from Everybody Hates Hitler), or the mention of him liking effeminate things, e.g. Black Swan, wearing his girlfriend's knickers, enjoying drama shows, which DOES NOT make you bi/gay, but if you were a Supernatural writer circa 2000-2010, you might think that liking girly things makes you gay.
That said, this is all very much still for-the-bit territory, and they had no intention of doing anything serious with it, so it was probably just to rile up Destiel shippers if anything. Like, the show (at least where I’m up to) has always banked on its All-American, macho, working class identity, and to have one of its leads be canonically bi might be seen as compromising that. Also it might hurt the pwecious wittle feelings of their 3 remaining straight, male fans (their original intended audience, as opposed to the weird GIRL audience they ended up with) if their favourite Cool TV Man came out as bi.
Having said all that, that is just what the writers’ intention was, and that cannot and will not stop me from reading it as something else (death of the author and all that)
I think Dean’s relentless flirting is partly because he does genuinely like hot lady and sex and all that, and partly performative, which is the case for a lot of things surrounding Dean in my opinion.
Like, Dean wants to get a good grade in Man, something that is both normal to want and possible to achieve, because he feels that’s what’s expected of him (no doubt in part due to Mr John Winchester, who probably had some feelings about how a man should conduct himself following his own absent father and time in the marines).
I also definitely choose to interpret it as Dean overcompensating. ‘How could I possibly be gay if I like woman and cheeseburger so much??? Look how much of a Normal Straight Guy I am, SAM.’ Because he doesn’t want to admit to the mere POSSIBILITY of being bi, to himself or to his brother, because he wants to be a normal, straight-forward, reliable Man, and almost certainly has some internalised homophobia going on.
Anyway, yeah, I think Dean’s womaniser streak (mostly) wasn’t SUPPOSED to read as covering up bisexuality, but I think it can very much be read as such. Sorry for the long rant lmao
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