I have a girl friend who is trans. Neither of us pass so well tbh, otoh she gets taken as female more than I get taken as male. I think if a woman goes to the trouble of wearing a dress and so on, they are *serious* where we could just be butch. Going out together in public is something of an adventure, and gendering, well people often just give up. I am lucky to be autistic so I don't care too muhc whether people stare or not. (BTW, I am 5'1" and she is 5'10".) People have always been polite, I was actually surprised at this. But I really have a good time with her and it has been great for us as we both understand the other I think. OTOH, as I transition more, and I will pass more than she will, not sure if it will continue to work. But we are just dating at this point.
Since I am early in my transition, I don't think too many people would understand my obsession with my gender the way she does.
BTW, I know there are transguys who would not go out together with other transguys for not passing. I don't like not passing mind you, actually I hate it, but I am also not going to live my life around it to the point that I wouldn't go out and do things with certain people because of it.
--Jay