I have been with several women over the years that made more money than I do and I don't think it should matter. However, if you can't afford to pay the tab, you can't afford to go out with the girl... When it comes to dining, I appreciate the purse reach from the woman as it at least gives me the impression that she is cognizant and doesn't just expect it. But, I want to pay the tab. Just don't get carried away buying her other more expensive gifts until it is a relationship and it is appropriate. IMO