If you do decide to meet with him, ask him and try to concentrate the conversation towards "about him" as people tend to like talking about themselves the most. You don't have to commit to sharing things about yourself either. It can be helpful for you if you sit down and make a list of questions you can ask him so when you do see him you are more prepared to keep the conversation more about him. If he has already talked about the people he doesn't care for he has actually given you important information about himself as he describes the interactions he has with these individuals that made him decide he doesn't like them. As you have shared "you barely know him" and the only way you can change that is by taking some time to write down questions that you can ask him where you can gain information about him so you get so you know him better. If you don't know what he did that resulted in him being incarcerated then tell him that and see if you can get "his" version. Always remember, all you are doing is getting "his" story and that doesn't always mean his story is based on the real truth. Instead, whatever he shares is how HE wants to see things. Also, you don't have to be "close" to anyone, not even individuals in your own family. You have a right to deciding for yourself who you want to share with and like and who you don't.