And in every case, we're meant to identify with the guy: He was attracted to her, and since she turned out to have a penis, that attraction was an intentional dupe on the part of the transgender woman.
To you it's probably never been more than a somewhat lazy, throwaway joke, but what the f**k kind of message does it send to young transgender kids? "If you flirt, you're a liar"? By society's unspoken rule, just hanging out at a club is an act of deception for somebody like me. After all, some guy might think I'm cute and approach me. If that person flies into a rage upon hearing the truth, society will be entirely on his side -- even though that rage may involve him trying to beat the s**t out of me, or worse.
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"Guys, they passed. These ones can be safely objectified and demeaned."
So for a trans person, that cloud hangs over every flirty interaction. I met a guy at a social event recently and got the feeling he might have been flirting with me, but I didn't know if he knew. I was scared a little the whole time because he was much larger than me (not that I'm small). I waited a month and a half of hanging out, without so much as a touch on the arm, before telling him. It took that long for me to feel sure I'd be safe either way. If you're saying to yourself, "Well, you shouldn't have led him on!" remember that some men consider simply being in the room with them to be "leading them on." You think I'd be safer wearing a sign around my neck? Some people are enraged just by the fact that I exist.