Perhaps you could ask:

1) Are there any artists that he hasn't collaborated with that he wants to collaborate with in the future? If yes, who?

2) Besides music, what other avenues of artistry would he like to pursue (acting, clothing line, etc.)

3) Does he feel like he's on track/where he wants to be professionally?

4) What is in his iPod right now/Who is he feeling right now?

5) Is there someone special in his life right now?

6) Most artists don't go on the message boards and stuff, does he?

7) Does he think talking about his Mom's problem has helped him heal in any way? How is she? What would he say to other young people who are in similar situations?

8) What's his favorite track on the album? Why?

9) What separates him from the other male R&B singers out there?

10) Ask him is there anything he wants to tell his fans (It could be anything at all).

I know this is a lot but maybe you could consider asking him some of this anyway. lol.