I don't think there's anything wrong with expecting someone to pay their own way. It removes any sort of financial pressure on the woman to reciprocate affection, and it gives the woman no incentive to lead a guy on just to get free dinners. A problem arises when there is a major discrepancy of income and the person choosing the date location is the wealthier. For someone making $300,000 a year, spending $100 on dinner probably isn't a big deal, while for someone making $50,000, it might be. So you should make it clear to him that you will pay your way, but the two of you need to decide on what's financially feasible for you. It's a compromise, and if he wants to live the luxury lifestyle, he can do it with his buddies and not you.
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