Answer:
Basically, anything about his past relationships (i.e. Why did your last girlfriend break up with you?)
Are you and your ex girlfriend still friends?
Does your family have money?
How much do you weigh?
Why do you like me?
Are you ever jealous of other guys that I'm friends with?
Why don't you work out more?
So, pretty much anything that you or any regular person might feel a little uncomfortable about answering.