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Dr. Susan: Ah, how the human spirit longs for simple answers to complex questions--rules of thumb, handy guidelines, a certain number of commandments, that sort of thing. I'm sorry to have to tell you, Dorothy, that when it comes to dating, flexibility and adaptability are the name of the game. For instance, let's assume you really like a guy and you know he doesn't make much money, and right now you have a pretty good job. Or you don't have a good job. Either way, after the first date or two, why not invite him on a picnic or to a cute new lunch place, or offer to cook him dinner? That may be less awkward than pulling out your wallet when the bill comes. The key to all this is to be yourself, and to be sensitive to the person you're dating. Do you assume, when you marry, that a man should and will be responsible for supporting you forever? Then don't offer to pay at all, and you'll only attract guys who want to take care of you and pay for you endlessly. No problem. But if you prefer a sense of equity, of being able to take care of yourself, of giving the impression that you're an independent woman, then speak up quite early on and suggest you split the cost of dates so neither of you feels unduly burdened. Then you can work out the kind of dates you both like to go on and both feel you can afford. No one should be working too hard to impress anyone else in ways they can't sustain over the long run. Let me point out, though, that a lot of young men will keep on paying, while perhaps resenting that you haven't asked to take a turn. Generosity, rather than abiding by an arbitrary rule, is a lovely trait in both men and women.