He was baffled but affable - he asked me, diffidently "So... is what you said the same as a sex change?" because he'd never heard the phrase "gender transition" before. I explained that it only is if you're a Sun reader

.
He also tried some standard-banter-for-middle-aged-women on me, but we could both tell that wasn't working, so he loosened up eventually (As did I, but then that's what I was paying him for).
Sadly, he lost points for asking me the inevitable "...but are you sure?"