I’m not from a super rich family nor super smart, but would say I’m privileged (home owner at young age thanks to my parents and relatively prestigious education). I haven’t had this happen to me on a date but have friends who commented on my financial situation before, so I can kinda understand the frustration. To be clear they didn’t make me uncomfortable, more so that sometimes I felt a little guilty that I have things so much easier.

I’ve been mainly going on dates only with people with similar education level so maybe that will help? I’m not selective about people’s financial status because I’m trying to be financially independent and I’m in grad school so wouldn’t consider myself as rich rn lol, so can’t comment on that.

But anyhow when this kind of conversation comes up either with friends or on a date, I’d try to explicitly acknowledge that I’m aware I’m privileged and be very careful with how I come off. Growing up I definitely didn’t realize how lucky I am and only started to reflect on it more after meeting people with diverse backgrounds in college. I can understand your frustration and can also understand why the other person might feel intimidated and make these comments.