I never get tired of Dean openly flirting with dudes.
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Let me put on my serious business hat for a moment, too:
The only thing that makes this inadmissible as evidence of Dean flirting with men for the heteronormative audience is the lack of the Male Gaze. In the grand tradition of visual story-telling, we’re used to the use of the Gaze shot in signaling desire and in this scene we are not shown the object of Dean’s flirtation visually. Dean is the object of the shot. And because the audience is not made to desire the object of Dean’s desire, a regular viewer will dismiss the possibility that the character desires.
Supernatural has the most awesome fucking people working on it.