I don't ask anything personal, it has to be offered.
I have had guys think it strange I don't poke and pry, I've always assumed it's safer not to ask unless they want to tell but you have to talk about something, otherwise it's a very cold experience. I usually err on the side of caution.
Never forget the time I asked someone about their family/where they lives(they'd already mentioned a bit of family stuff) and touched a raw nerve. It was a completely innocent question

and went somewhere very sensitive.
Some guys love to tell you about themselves, sometimes it'll be true, sometimes not.
Found out after some years that someone had more than exaggerated something until it was a lie, and they would have a good idea I'd have seen the proof so not a clue why they continued the same lie - this really made me think because I'd shared quite a few personal things with him.
If someone asks I'll answer but there are things I don't tell, things I keep guarded, they don't know if it's the truth or not and sometimes people don't like the truth and want something far more glamorous, I decide what I am going to release but I'm generally fairly forthright with it.