I'm of the personal opinion that it never hurts to ask someone you care about those questions. I think articulating you care about him, that you know he's going through a hard time, that you don't always know what to say but want him to know you care, etc is a good place to start. I don't always return calls and emails from my mentor because I feel all dark inside, but just knowing she is thinking of me helps. (She's not obnoxious with it- just a vmail or text every few days, sometimes with an offer for me to come sit and just talk). You sound like a good friend. Ask him what he needs when he is in those places and then listen and respect his wishes. ++