The next one was my roommate in college. She and I were friends before becoming roommates, but things between us started to sour as politics crept in and I complained about my internet pooner friend. She was a lesbian, but told me she was conflicted because her ladyfriend whom she had a crush on transitioned to being a man but she still had feelings for her (and I guess they got drunk and hooked up), so she wasn't sure if she could still call herself a lesbian. I told her that she definitely was still a lesbian. A few years after college I found out she transitioned.
The next one was a guy I knew in grad school. He was very tall and handsome, the spitting image of a stereotypical Native American with long black hair. He was also a furry and was at the very least bisexual if not gay. I talked to him for a few years after grad school and in around 2015 he told me he was going to become a woman. Again, I had no idea what to say that wouldn't be bad, so I was like, "Uh... congratulations?" I later lost touch with him because his posts on twitter complaining about Native American discrimination were annoying the fuck out of me.
In more recent times, like within the past few years, I've seen a few. The Ulta I go to has a couple of troons working there, but they have been nice for the most part. I went to the grocery store and saw a man who was probably 6'4" and balding, but was wearing a dress. I steered clear of him. I've seen people with pronoun pins working at the grocery stores too. One was a very obvious man whose nametag sad "Jacqueline" or something. Another was a very obvious girl who had a giant THEY/THEM pronoun badge.
In 2020, I went to outpatient therapy for eating disorders over Zoom. It was the biggest waste of time ever, and frankly I should have walked out the minute I knew they were entertaining delusions. Everyone had to introduce themselves with their name and pronouns. I went along with it because I knew that protesting it would just waste time when I wanted to actually utilize this therapy to get better. But there were a few girls in there who had "he/him" pronouns.
A couple years ago at a friend's house, I was chatting with a guy and he mentioned "Alexi." I asked if Alexi was his wife because I am lonely and desperate and trying to find single men. He looked at me oddly and defensively said, "My boyfriend!" I kind of stammered and said, "Sorry... I usually hear that as a girl's name."
I later met Alexi and found out why she had that name: she was very obviously a girl who demanded that everyone refer to her as a man. (Sidenote, I actually did meet a man with that name a few years prior. But still.)
And finally, a couple weeks ago I was at a convention. I met this one chick who was GROSSLY obese. Like, gigantic. Probably edging close to 400 pounds. She was wearing a mask (of course), and was overall just a very bitter person. I talked to her a bit and I noticed the trans stickers all over her water bottle. I asked if she had been to this con before and she said, "Well, technically yes, but I had a different name then." I realized that this was probably a guy. However, I wouldn't have known it otherwise. The voice sounded feminine enough and the mask covered up any obviously masculine features. Plus, being that obese will often add androgyny.