LOL he just told her she'd be pretty if she smiled more. What an asshole. Being an asshole, to an asshole. There's no winner in that exchange.
I have a theory that JKR got sexually abused by a trans woman who had won and then abused her trust, and hasn't processed the trauma from it. And doesn't want to, nor feels she has to. So she just decided to hate that whole class of people instead.