I guess I’m not racist… my first thought was “a pilot, obviously”

Highly disagree with that. Just because the trans person is ok with their identity doesn't make it ok to assume others are too.

I'm all for trans people being trans, but it's a very key piece of information for a lot of people, especially where sex is concerned. For example many people only want to sleep with those of the opposite biological sex and a person's gender identity means squat. There's nothing transphobic about that; it's how the vast majority of the population realistically looks at the intersection between sex and gender.

Again, that's not to say trans people shouldn't be allowed to feel the way they feel, and the vast majority of people do support that. But if they're going to be dishonest with people and do things that are likely to cross other people's boundaries, that's another issue altogether.

Umm not having that conversation first is one of the least transparent things a person could do.