Don't put too much expectation or energy into your first punt being "perfect". That's a lot of pressure to put on both yourself and the escort. If you add that to the normal first-time nerves, it's a recipie for disapointment. Been there, done that.
Pick one of your top 5, and dive in. If it's a good meeting, do it again. If it isn't, move on. We are blessed with lots of fantastic ladies.
Find someone you click with - it's worth it.