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Small-Scale Question Sunday for March 19, 2023

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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Yep. One of my friends was a standard fat gamer programming nerd until the pandemic. Funny, if a bit incel-y in personality (he made some occasional sexist comments that were annoying but not fatal to our friendship). During the pandemic he finally lost the weight and I was thinking "Hey, maybe we can finally get this guy a date. Funny, decent job, tall enough, starting to look like a viking" I wouldn't date him myself for a couple of reasons, but get some good pictures for an online dating profile and we can improve his quality of life a lot (he's prone to depressive episodes and loneliness).

I brought up the topic and he said "actually, I'm not thinking about dating at all right now because I've been seeing a gender therapist for a year." We've hung out five or six times since then (over two years), with each hang out getting more uncomfortable and creepy, and now I'm dodging his calls (I'm not misgendering btw, he's never formally asked me to change names or pronouns). Somehow "man wearing a dress" freaks me out less than "man wearing a dress and boobs." It's much more 'it rubs the lotion on its skin'. He did finally (briefly) date someone (an older woman) during this process, but broke up with her because she obviously saw him as a man.

So yes. We're not close enough for me to suck it up and lie and not distant enough for me to just be polite. Hence the avoiding.

You say you're not going to "suck it up and lie." But then why do you say one paragraph before "I'm not misgendering [my friend]" because "he's never formally asked me to change names or pronouns?" Would you capitulate to that request, if he were to make it? Wouldn't accepting such a request also be lying?