I am both ways on it. On the one hand, I believe every human has a right to hold certain things to themselves. On the other hand, my daughter gets herself all tied in knots over stuff, and when I try to help her sort through them I can’t crack that nut open, so she broils. If someone is suffering because of something they are not ready to share, the ones who love them can see it. We hurt, watching someone we love turmoil alone. It is natural to want them to open up so that hopefully we can help. Perhaps you could tell him that you don’t feel okay talking about what is bothering you, but if he doesn’t mind, maybe talking about something else would help. Getting my daughter to open up sometimes goes better if I start talking about something of myself, maybe from my teens, or early adult uears. I will talk about some silly stuff, then ease into more tense subjects. Usually that will set a tone that lets her feel more comfortable to bring up her own topics. There is nothing wrong with having certain things to keep to yourself, but those who love you can’t help but want to know what is hurtful to you.