Here's a game I started trying out this past week. It's called Top Three.

This is how I introduce it-

Hey, let's play a game; it's called Top Three. You'll name a topic and I'll pick my top three. You get a follow-on question and they we'll switch. So, for instance, if you picked pizza toppings, I'd say "Italian Sausage, Pepperoni, and Bell Peppers." Then you'd ask something like, "Bell peppers, really, why not go all pork and pick Canadian Bacon?" There are three rules. Answer honestly, be non-judgmental, have fun.

I played it with a girl over dinner and didn't have to worry about coming up with stuff to say the whole 90 minutes we were together. It was a D2, so we already had some level of interaction. It went great with her.

Later that night, I met some friends in a bar and tried it on a girl much younger than I. She was a trooper, but kinda lost interest because I hadn't laid the correct groundwork.

A few days later in another bar I tried it again, same situation as the first.