I once dated a guy and he just voluntarily told me about his past. And my thoughts were, "And what should I do with this information? Does he want me to respond to this in some way?" Maybe he wanted me to tell him about my past also, but I didn't do it. He never asked.

If I'm dating someone and he's already asking about my past, it speaks more about his insecurities. I think if you are a confident person, man or woman, I'm not sure if that question is necessary to ask. But this is my personal opinion.