Oh gosh. Ben, you are super charming. I know so many mid-twenty something virgins. Heck, I was one. I remember it seemed like a big deal at the time, but in retrospect, it wasn't. Social scripts are great for first interactions like first dates. You just need a flirting script. Thankfully, we have the wonders of the Internet! The SIRC Guide to Flirting has got you covered: http://www.sirc.org/publik/flirt.html ... The small of the back is a fairly bold starting move. I'd go with touch on the shoulder, touch on the hand, handholding, etc... There are lots of lovely people who don't rely on sarcasm to seem interesting. Someday you'll meet that person who is confident enough to be vulnerable and trusting instead of sarcastic.