In most cases, I haven't really had much of a problem with paying for my dates. But the bills have to stay within reason, of course. There was one broad I went on a few dates with a couple years back where two dinners racked up around $100. Even then, this could have been tolerable if we wound up having sex (we didn't). On the plus side, she did invite me to a naked pool party and I got to see that at least (fantastic body, but ugly ass face).