Since you've already let him know you are willing to talk, I wouldn't go there again. Not now anyway. What I would do,if he does talk, I'd figure out a way to reinforce it.
What would you say to a male friend that opened up to you about something very private from his past? I would say something like, "Wow, that's some really big stuff you're carrying around. Says something about you that you've been dealing with all that and coping with life in general too." At least, that's close to what I've said to some of my men friends in the past when big stuff has been shared.
You're idea about shooting pool is a good one. It's not as "intimate" as walking on a beach, yet there is room for convos to happen. Just let him start any convo that has anything to do with him. Keep any banter light and fun. I use this type of thing all the time with my D's. Really helpful.
