Thanks for writing to Just Answer.
I don't think it's mockery, I think he has been burned very, very badly in the past by a woman .
It sounds like he is trying to see if new women he meets are anything like her...and if they are, he will most likely not get involved.
And I do think it would be fair to turn his questions around on him...you might find out some interesting information to help you make your judgment about whether he is a good relationship risk for you.
If he is that persistent with the questions, look into his background. You may find red flags when he starts talking about his past relationships. If everything is everyone else's fault, and he doesn't admit to any shortcomings himself, proceed with caution!
His questions don't reflect on you....they reflect on him.
Hope this helps! If it has, please click on ACCEPT