I like the idea and direction of that, but a few issues. Namely, Alex, by all accounts, pretty much looks female. If she neglects her appearance, she could pass off as androgynous, but considering she identifies as female [i]and[/I] cross-dresses, many would assume that she's a girl anyway. She isn't exactly averse to telling people her biological gender -- but the actual topic would have to be brought up by someone else, and they would have to be reasonably close.

Realistically, Brent would have to be told by someone else. I'm also not sure what you mean by 'previous research'.

If, however, he found out and questioned her about it, she would probably try to be as accommodating to his queries as humanly possible -- however, it would also make her rather uncomfortable. She also probably wouldn't have the guts to ask him to stop, meaning, yes, he's probably not going to endear himself to her.