I think part of the issue in general is how the roles of men and women have changed, which in many respects conflicts with the more conservative stance some here share (including myself). For example, you hear about women wanting to be treated as equals, women equaling/exceeding men financially, etc...
(all things I have no issues with) but then some of those very same women expect special treatment b/c they are women. So which is it, you want to be treated as equal or you want special treatment (or you want both as long as it benefits you). Something doesn't quite jive with this. On the other side, you have some here claiming that a guy's "trustworthiness" is based on his willingness to pay for dates, or the real doosie is claiming that a guy should always pay to simply avoid giving a woman too much power
I do wonder, for women who are doing well financially, is there some sort of sliding scale as to when you should offer to pay or contribute (not factoring in marriage or maybe a LTR where your finances are all commingled), or is it basically "You aren't a real man if I have to ever pay".
Unfortunately, if you expect that a guy needs to wine/dine you indefinitely, then you can't complain when he has an expectation that this should lead to sex.
All you can hope, is that both people are honest about their expectations, lay the cards out there and see where they fall, instead of playing games based on your own personal expectations.