"What does your mom think?/Is your mom dealing ok?" And "Do you think this will make you happy?"
I am honestly fortunate enough to be surrounded by extremely supportive people. So far, the worst reaction I've received is some co workers ignoring it, but since legal stuff has started, they've been much better about it. I have no idea how I'm going to react when I inevitably hit negativity. Even when my mom wasn't being supportive about transition, she was trying to get me to counseling for my depression and gender questions. She was just concerned I hadn't thought it through enough (which, given how impulsive I am, is a legitimate concern).
And then, there's my brother. I told him last year. He forgot. Asked no questions. Fat forward to July.
"Brother, I am becoming manly. Male pronouns plz."
"Huh?"
"I told you about this. I know I did."
"Oh, right. The trans thing. Is that an official thing now?"
That boy I swear.