One of my favorite get to know you questions is "what would you do if you never had to work?"

Shows a lot about a person, in my eyes. How would they be spending their life if money was never an issue? I think it's important.

Also, not to make too many assumptions, but since you just got divorced, I imagine you know many more things that do and dont work for you than you did 5 years ago. I would tackle it from that perspective.

I got kinda nervous for that same reason with this last girl (current GF) but then I looked back at my past relationships and realized that I do have standards and don't want to trick myself into thinking everything is peachy when I know something will bother me down the road. Don't be a dick about it, but realize that there are many similarities between pre dating and an interview, but its not the same. If you can't honestly think of anything to ask her that means there is nothing pressing that you want to ask, thats fine. Just talk about something else. 4 hours should have given you enough go-to topics in case you get stuck, AND given you a good idea of some of what shes interested in.

Those, and then when you find some in common expand on it. Or a genuine dislike, even if she hates something you love it can make for good/interesting conversation. Instead of going for a list of questions, just go for topics to chat about other wise you will run into a lot of dead air and feel like drill sarg's.

That said, meh I hate dating. Last spring I went on a few blind dates and it really does suck trying to strike up conversation with a stranger when you're rusty. Movies are always a safe topic I discovered, love them or not into them, there is still some you've seen that you can share a laugh over.

 

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