When I imagine asking him, "What don't you ask questions about my life?" I assume I'd get a response something like, "You can tell me anything," or "I'm open to hearing what you want to talk about," or "You're free to talk about anything."
If I had to devise a quick mental model, it might seem like the difference between talking at someone vs talking with someone? I might have to think about that a bit more. Do you have any insight here?