Had this same problem with a friend I saw some four months after I had figured out I'm trans.
"Are you sure?"
"Maybe you are actually __"
"Have you not thought even for a while that you might be wrong? I recommend you think about that possibility!"
"You are okay as you are."
"You don't need to feel dysphoria."
"You're always being so radical, is this just about you hating men? You should not hate men."
He seemed hellbent on asking every infantilizing question anyone has ever invented about trans people. That was one very very very strenuous "conversation"!