Sounds like Bacon has the best tack here - play the polite concern troll and say stuff that's hilarious to anyone with an ear for dry humor. "I didn't know you were into big girls. I guess I should be happy you've found someone who likes you."
Although if you wait until he's drunk, he might shrug off the conversation once he sobers up. I say do it after a relaxed meal with him.
Although if you wait until he's drunk, he might shrug off the conversation once he sobers up. I say do it after a relaxed meal with him.