The no win situations:
Where would you like to go to for dinner?
I always picked the wrong thing, he either just had it, or didn't like the place, or I wasn't telling him what I wanted, that I was trying to think for him.
What movie would you like to go see?
Again, always got that one wrong. I would pick a movie that he would like, got yelled at for picking some thing for him, so I would mention a chick flick, got yelled at for that, because how is he supposed to watch that trash.
I still to this day freak out with those trick questions, even when I know my friends are seriously not trying to "trick" me, I get panic attacks over them.