7x20. The Girl with the Dungeons and Dragons Tattoo.
(Look at how confident Dean is in the first gif that this will work, though - and flirting your way through security, that’s not something you’re sure can actually be done unless you’ve done it before, because with the lives they’ve had, the Winchesters are painfully aware of the difference between movies and reality. So, no, Dean knows exactly how to make this technique work - because he’s used it before. And how many women work in this field? Police, security guards, bouncers? Mh.
So, again - the fact Dean can flirt with men doesn’t mean, in itself, that Dean actually likes men. Dean is a liar and a conman, and finding a way past security guards is simply a part of his job. But considering everything else we know about him, and - mostly - that TV narrative is very different from real life - yeah.)
Yeah - and in this episode Charlie is used to knowingly establish that false premise that you can only flirt with the gender(s) you’re interested in…
Yep. It wouldn’t actually mean anything that Dean routinely used flirting in order to get past security guards, because yes, he is a con man and it is part of his job. Except Charlie’s insistence that the lack of attraction to a particular gender makes said flirting inherently impossible, requiring the intervention of someone who does have an attraction to that particular gender. And Sam and Dean BOTH just roll with this rationale as if it’s a completely valid premise.
(and note, it’s not Sam who walks her through flirting with the dude, and it’s not Sam who we routinely see flirting his way past security guards, bouncers, and male police officers throughout the series, either… Sam prefers sneaking, bluffing, and assuming the guise of an authority figure in order to talk his way through these situations– or straight up lost-puppy innocent bumbling and apologies. Dean’s FIRST thought, his gut instinct, is flirting.)
(because again this is how Sam and Dean differ. Sam attempts to baffle obstacles by “selling himself” to them with puppydog eyes and logic, while Dean attempts to baffle obstacles by “selling them to themselves.” Aka, flattery and flirting.)