I think it's a pretty different case than model trains, though! To use myself as an example - I'm a non-binary person who was female-socialized and has never developed any skill or interest in makeup, and I've also never gotten into model trains. But one of those things has been enough of a culturally-dictated Presence in my life that I have had to make choices about it (and defend those choices, and endure the opinions of other people on those choices, both directed at me and as ambient sexist commentary) - and it's not the trains.

LW has gotten as far as figuring out the issue might be Fraught. Points for that! However, he hasn't gotten as far as realizing that his gf's personal opinions re: makeup are much more relevant to his actual question ("can I ask my girlfriend to wear makeup to please me on our dates?") than any advice columnist's opinion could possibly be.

I guess part of what I was boggling about, re: alienness of worldview, is that bringing up "Makeup: Fun Toy or Patriarchal Scourge?" as an abstract issue to discuss seems perfectly reasonable to me, and much *more* reasonable than cooking up indirect scenarios that might possibly cause her to volunteer some useful information, while carefully avoiding letting her know that there is specific info being sought. That seems like so much work, and so likely to blow up in someone's face!