I had to think of your friend saying it was basically ok to be a crossdresser (even if not the right terminology) means he is one himself, know someone who is (other than yourself) or an admirer! Obviously I have no way of knowing but it did make me wonder because of his statement. I do think we often give off signals, without us being aware we do so, that those being observant or more aware of certain traits for whatever reason, will pick up. In any case I hope it works out to your favor!
Dana