lol. That's weird because I am sometimes the one who shares things with my friend that he verbally tells me is annoying or he's not in the mood to listen to. But he also shares so openly about many things, that I get the idea that he's trustworthy---not having some ulterior objective. I almost always listen to him, but sometimes I'm just not interested as much in the same things. But we really get along very well in person. I think trust and openness are the most satisfying thing.
You might try asking him to say what he thinks but in a gentle way and then be less direct and allow for a lot of pleasant, quiet interaction time before you expect him to share what he thinks. Also, positive remarks, though perhaps manipulative from your perspective, can be very helpful if the remarks are genuine.