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When I was dating, I always paid for the date or at the very least my half of the date. Very few men were upset by it. However, the bf was one of them. It took him a bit to get used to me paying for things. I held my ground and he has worked through that little "caveman" part of his thought process. I make a great deal more money than he does and I think it is only fair that I do more of the paying.