morgan - Great advice given by all. The only thing I would add is to avoid say, "Is anything wrong?" Let him ask that of you.
Seriously, the mere act of asking that is pursuing. Try (as hard as it may be) to act "as if" everything is OK with him. Be prepared to say, "Gee, I had no idea anything was bothering you. You haven't said a word to me about how you feel regarding..." and fill in the blank.
Let's make them do the heavy lifting from now on. OK?
BTW, although I am from Ohio, I am not a Tribe fan. But I see Wakefield has a no-hitter going into the 5th inning... hmmm