Yes, I agree that the "I'm going to management" remark is a little unusual.

It's hard for me to get a read on this situation, even though you have done a good job of explaining it.

This is a weird question, but where/how does this guy live? On his own?

I think that you should think hard about what you would want if you did get closer to this guy. Would you want a boyfriend? A husband or partner?

I'm also curious about the relationship that ended in court.

I'm getting a Pandora's box sort of vibe from this situation, and I have no idea if it's warranted.