Yeah, I wasn't really thinking of it as elaborate indirect imaginary scenarios, but more that if he really is interested in makeup in a way that isn't purely patriarchal, those are things he should look into anyway! (And if he his interested in a way that's purely patriarchal, he should explore the things those questions bring up anyway.) And if she is someone who's sensitive about the question (he clearly already is), it's still tough for me to think of how to bring up "Is Makeup Patriarchal?" in a way that 100% doesn't sound like I'm commenting on her choices or appearance. "Makeup (abstract) is something I enjoy and am interested in" feels different to me - and if it is something he enjoys and is interested in, he *should* explore it in contexts other than already applied to his girlfriend's face.

I am a female-socialized-and-appearing person but I honestly go years at a time without thinking about makeup as applied to myself, and probably do spend more time on model trains. There definitely is a difference here between "Would you like to help me with my model train setup?" and "Would you change the appearance of your body for me?" - and he's realized that one of them is much more fraught! Her opinion does matter more about the second one. But the only reason it matters is that he's interested in it - if he also didn't care about makeup, why would he bring it up? It wouldn't be his business unless she wanted to talk about it, anymore than exactly what clothes she chooses to wear or whether she dyes her hair.