Bi!Dean: Origins
Rewatching the Supernatural pilot episode today, there’s a line that stood out to me that I’ve missed on previous viewings. When Dean is arrested in Jericho and the Sheriff is interviewing him, they have this exchange:
SHERIFF: I’m not sure you realize just how much trouble you’re in here.
DEAN: We talkin’, like, misdemeanour kind of trouble or, uh, squeal like a pig trouble?
“Squeal like a pig” is a verbatim quote from the film Deliverance, making explicit reference to male rape, which is hardly comic fare - except that Dean is smirking as he says it:

Earlier in the episode, Dean mocks the Jericho police for their lack of leads on the case, calling it “exactly the kind of crack policework I’d expect out of you guys.” Deliverance is set in the Georgia backwoods, while Jericho is in California, and as such, there’s an element of insult to the reference here: Dean is basically calling the the Sheriff a hillbilly.
But given the framing of this shot - the Sheriff looming as he pulls out a chair in the foreground, Dean small and smirking up at him from the back - it seems plausible to argue there’s another element in play here, too. Eric Kripke, the show’s creator, who wrote the pilot episode, has acknowledged that Dean was both named after and inspired by Dean Moriarty of On The Road, who was bisexual both in Kerouac’s fiction and in real life, which makes the question of Dean Winchester’s bisexuality a valid question from the off. If all Kripke - and, by extension, Dean - wanted to do with this exchange was insult the Sheriff, there are any number of other references, cinematic or otherwise, to have chosen from. Instead, we’re given this one, which arguably casts not only this exchange, but Dean’s arrest, in a different light.
Earlier, when the Jericho police confronted Dean about his fake IDs, the arresting officer asks him, “You got anything that’s real?”. To which Dean, grinning, replies: “My boobs.”
And then we get this shot, just to round it out:
Thus: in the course of his arrest, Dean makes two overtly sexual comments to male police officers in conversations that were otherwise devoid of sexual overtones, one of which feminises Dean, and the other of which references male rape, though his delivery renders the impact somewhere been banter and innuendo. We’re also shown him smiling as he’s bent over a police cruiser, the camera zooming in on his expression, and as with his subsequent interview, the framing of this shot is suggestive in its own right.
How, then, does Dean behave around women? Consider his earlier, similarly loaded exchange with Jess, which is usually taken as establishing Dean’s particular brand of straight,overt masculinity. If it’s reasonable to assume that Dean is flirting with a woman he already knows is taken, when her partner is physically present, and who he has every reason to think won’t be interested in him, then it seems just as reasonable to assume that he’s flirting with the Jericho deputy, Jaffe, who’s equally unlikely to reciprocate.
As such, it’s worth comparing the two conversations - and Dean’s reactions to them - in greater detail. Speaking to Jess, Dean says:
DEAN: Oh, I love the Smurfs. [Referring to Jess’s tight, cropped shirt.] You know, I gotta tell you. You are completely out of my brother’s league.
JESS: Just let me put something on.
DEAN: No, no, no, I wouldn’t dream of it. Seriously.
And here’s his grin as he wraps the exchange:

By comparison, here’s his exchange with Deputy Jaffe:
JAFFE: So. Fake US Marshal. Fake credit cards. You got anything that’s real?
DEAN: My boobs.
And here’s his grin as he wraps the exchange:

In each of these shots - with Jess, Jaffe and the Sheriff - we have the person Dean is addressing shadowed in the foreground. In each of these scenes, Dean makes a sexually loaded comment, then grins at the other person. And in each of these scenes, there’s a power-play going on that Dean is attempting to manipulate by making things sexual: with Jess, he’s insulting her so she’ll happily leave him alone with Sam; with Jaffe, he’s distracting the deputies from asking about his brother; and with the Sheriff, he’s maintaining an air of bravado while under arrest. Yet, thanks to heteronormativity, we only take the exchange with Jess to be representative of his actual sexual preferences - even though, in context, she’s the person least likely to act on the flirtation.
On the basis of all these things together, I’d therefore argue that Dean’s bisexuality has been implied since the pilot episode, and continues to be implied - and, at times, outright stated - for the next ten seasons. In fact, I’m almost tempted to do an entire Supernatural rewatch just to prove the point.
What say you, internets? You game?
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