LOL My bf is the chatty one but for a long time he kept it on the surface. We both have trust issues, so it's taken us a long time to even get to the level where we are now. I ask him questions and that seems to help him open up. It's like he doesn't know how to ease into deeper discussion, but he'll follow my lead. Basically, I give him little nudges and then shut up and listen. The more outright and blunt you are the more likely the person you're talking to is to respond in kind. To be trusted, you have to trust and to expect honesty you have to be honest. You could say something like "I feel like you're having trouble talking to me. Is there a reason this is hard for you and is there something I can do to make it easier?" Just do little things to shift the focus unto him in ways you can both be comfortable with.