With the OP being so awkward and having issues going on, I doubt he will be able to tell the difference from she liking him or just trying to get money. But if he is having a good time, not sure it really matters as long as she isn't totally draining his wallet dry. Go on the fucking date. Movie tickets, popcorn, maybe drinks afterwards is better than sitting at home doing nothing. Get some life experience! Have a story to tell.
I know it is hard to imagine, but some strippers/escorts do actually like going out without money being involved. Maybe she thinks the OP is nice, could have a nice relaxing time with him or maybe she is trying to extract more money out of his wallet. Only one way to find out. Either way he gets a movie with some nice eye candy on his arm.