3. Do my clothes make me look fat?
He knows that this is a trap. If he says yes, then he’s going to have to deal with the wrath that you give him for calling you fat. If he says no, then you might call him out on being a liar to save you from your feelings. No one wins here.
4. Are you sure that’s the smart thing to do?
Even if you think that he’s completely stupid about a decision that he’s going to make, you need to be more sensitive about letting him know about it. Don’t resort to passive-aggressive remarks such as this one. It’s only going to infuriate him and make him want to do it even more.