So after we hung out the first time, I asked about 7 times after only to get replies like, busy, tired, no thanks, etc. I did ask if she wanted to hang and she said yeah, but never bothered because "inconvenient" because of the distance, even though I iterated previously that I have a car and am willing to drive that far because it's normal for me. The only reason I wouldnt say "hey I see your OKC profile says you wanna hang" simply to avoid what people generally consider stalkerish behavior. — Greg 31 secs ago

So I did ask her "Stacy, do you actually want to be friends?" And she replied "are we not?" And we had some back and forth which she agreed if I wanna do something, let her know and we can. Overall, our relationship is really weird and I have no clue how she interacts with other friends but I said "all we do is complain about stuff to each other via text" and she said that's basically the same for all her friends. So not sure if its completely normal for her but it's still unconventional. It's just the way things are, in 10 years if this continues, our "friendship" would be meaningless. — Greg 1 min ago

This will have effects opposite to OP's desire not to worry his mother. Obviously if the objective was "how do I inform my mother, regardless of the effect this might have on her and our relationship?", the solution would be very simple — Alexis 53 secs ago

Great answer overall. However, many transgender people find the use of "transgender" as a noun to be dehumanizing and offensive. "Trans(gender) men/women/people" is a much better alternative. See here: glaad.org/reference/transgender — ekl 57 secs ago

The second paragraph here is wonderful. Don't ever ask someone out in a situation where they can't leave (while they're working, while you're in a elevator, etc). It's not a Lady Zoo. She's at work. — L.S. Cooper 2 mins ago