I think it depends on the how you ask the questions and what questions you ask. I'm not suggesting the first degree but questions that help him realize that you care, are trying to understand and want him to be happy.
"you're really confused, that must be difficult. Is there anything you need from me?"
And then stop talking, become comfortable with silence. he may or may not talk but you've let him know you're there and hearing him.
You're not questioning for any reason other than to give him the opportunity to talk and you to listen.
Me 57/H 58 M36 S 2.5yrs R 12/13
Let me give up the need to know why things happen as they do. I will never know and constant wondering is constant suffering. Caroline Myss