If the date is a real dead end, then I will cut my losses (e.g. call it an early night) but overall I'm not thinking about money if things are going well. I certainly don't have any expectations about her paying and if she offers and insists in any way I sort of take that as a negative sign if we are just starting out. In my experience, that means she doesn't want to feel obligated in any way, but that's only happened maybe twice that I can remember.

It's also situational, of course. If I am taking a chick from around the way out, I don't expect her to pay for shit ever. I know ya broke, fantasizing like Mariah get a grip on my bumper and rub ya clit on my tires (c) Too Short. But if I am with a girl from money and/or with a good job, yeah at some point I'd like to see her come out of pocket for something just as a gesture.