I really appreciate how thorough this is. I think you are right. I have been very gentle with telling her that I am content in my womanhood since I do worry about upsetting her, but I suppose it is within my right to be honest if she is upsetting me. She is a really good friend when we aren't talking about all the gender stuff though.

No problem! I hear ya. I have often struggled in the past with asserting myself. But, I think of it this way: A good friend cares about me and wants what's best for me; someone who cares about me wants to know if I feel hurt by something they say. We might not always agree but I can trust them to care about me and to actually listen to me. And, moreover, the phrases I stated (not saying you have to say those directly! just as examples) are not being mean. They're just statements about the truth, and I think they're all consistent with respecting your friend's experience and identification.

If your friend gets upset when you set a boundary-- well, a boundary is a boundary. It's OK for her to feel whatever she's feeling, but once you set that boundary, it is NOT ok for her to keep breaking it.

I don't really have other options though, since I know I want to go to a selective liberal arts school and they are pretty much all the same in terms of being woke and social justice hotspots.

I wouldn't say that's necessarily the case! Are you in the US? Liberal arts colleges in the US are generally be predisposed to harbor TQ+, but I'd say there are a few that are a lot worse than others, and probably some that are more relaxed than others as well (again, region really plays into this).

Anyway, if I may ask, do you know how bad things are with non-STEM classes/humanities classes? I am good with science but I kind of hate it so I was considering studying history/political science since that feeds well into law school, but I realize that poli sci probably attracts a lot of woke people.

From my experiences talking to friends, poli sci is kind of a mixed bag, a lot are far left but some are far right actually, haha. My experience with humanities classes was that many had a very liberal perspective, e.g. messages of equity, but there was relatively little mention of gender identity nonsense; if it ever affected discussion pertaining to demographics, it was almost always about race. (And those discussions tended to have way more nuance than the echo-chamber posts I see on Reddit.)

There are actually a couple of users on this sub who are/were in law school; if you're interested, I can PM them and ask if they'd be down to talk with you about it. But, whatever the case, you should pursue something you're interested in and not STEM just for the sake of avoiding TRAs! My field has its own problems, lol.