So I've started doing this on first dates... I ask the girl how the date is going for her. I don't do this awkwardly at the beginning, but I've been on a few dates that lasted a few hours of talking and was getting very positive and interesting conversation. Recently, we were at the bar till it closed, and only had 1 drink each.

At one point during the convo - I leaned in and casually asked her, so what do you think of tonight. It was met with some relief, I think she really enjoyed answering the question, and then i segwayed her into telling some horrible date stories... We traded a few which helped us each demonstrate value. I was able to tell her about girls I rejected for funny reasons, and she told me about the kind of guy/stuff she's totally turned off by. Great - a manual for what not to do on a date with this girl.

Another quick and low-key version of doing this, would be to ask her to tell a horrible first date story... but I really like the thrill of asking her bluntly what she thinks of our chemistry in person...