Think of a boy as a human person. What would you talk to your cousin about; what would you talk to the older couple next door about; what would you talk to someone that you were working with on a church or school committee about. The best thing is to relax and practice being yourself. Boys aren't comfortable when you act phony. Now, the questions to ask; don't ask too much, because if you're trying to get a look at his character or personality, whatever he tells you may or may not be true. Keep it simple; ask if he has any extra curricular interests; does he like books or movies, if so, what kind he likes; does he have brothers or sisters. Don't go farther than this, you may look pushy or needy. Just relax and let him tell you about these things.