Most Helpful Guy
Ask about his work, family, sports he plays, or watches, if any. What he thinks about politics - though don't get too much into that. What does he do in his spare time. Try to do some active things together, and it will give you a different perspective than you will get seeing him as just an observers. And ask him his favorite sex position, how long he is, and how long he lasts. (Just kidding) Ask if he's ever had pets, what he liked about school, or disliked. Get into some general subjects about whatever, so you he doesn't feel bombarded with a hundred questions. And ask what foods he likes, and what restaurants, etc. And ask him how he feels about relationships.