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It is a very good question. I have been dating my girlfriend for two years and I still get bad feelings when I let her pay for things. It is very touchy because you don't want them to get too used to you paying for things all the time because then they will just assume it is going to be done.
who goes on dates? and who is ashamed to let a girl pay for you? Is this the 1950's?
I emphasize with Patrick. I'm uncomfortable letting a girl pay even after knowing her for a long time. Unless she strongly insists on footing the bill, I'm paying.