First, Orleans didn't mention it, but if you go to his blog, a couple months ago he posted something about conversation that may be useful.
Second, to build upon what he said here, when you are calm, and focused outwardly on the girl, you will listen to her. When you truly listen to her you will be able to respond to something she said. So in your example, she said the girl with her was a friend. So make a statement about friendship. For example, "Cool, I'm here with my friend too. We always have the best time when we go out. Especially when we come here. Don't even as about the crossdresser conversation we had here a couple weeks ago. So what is your best story of being out together?
That question along with good, friendly but strong eye contact, should compel her to give you a story that should get the ball rolling so that she is doing a decent amount of the talking.
Also, listen to your natural friend and get comfortable saying exactly what is on your mind. That means expressing yourself fully and saying, if you run out of stuff to say, "Darn, you are SO cute, you are making me nervous and run out of things to say. I am so mad at you right now (this and the remaining last part with a sly smile). Just for that, I'm not talking to you any more
Our relationship is over
I'm breaking up with you as my conversation partner