My favorite ice-breaker, ever, is exchanging the worst jokes possible. It eases tension and removes a lot of the awkwardness of meeting new people. Plus you get to laugh. Who doesn't enjoy laughing?
I've never been on a traditional first date except with my fiancé. Everyone else I ever dated, I've already known decently prior to the first date, so we just continued our hang outs away from our usual places.
With that said, my fiancé and I are, well, "unfiltered" when it comes to conversation. We shared some insane jokes and it turned to honest chats about something related.That's what made our date so successful. We just said what we had in mind and felt no obligation to try and impress one another. We learned as we went. It helped that we were both adults and off work on the same day. No need for planning or worrying about curfew. It was all spontaneous and lasted the entire day.
Being pleasantly surprised at discovering common interests first-hand is much more amazing than just talking about it.