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Dr. Susan: The first thing you need to do is determine why you want him to spend more money on you. Is it because in your background you learned to equate money with love? Or is it because your boyfriend truly is a cheapskate? If he's very miserly with you for no good reason (low income, saving to start a business, helping his aged mother, etc.), it could be a sign of a person lacking generosity in other ways, too. Many relationships flounder on the issue of money. If you're serious about him, you need to have a few conversations about what money means to each of you. If it's a matter of not being able to go to places you long to go with him, I see nothing wrong with sharing the cost, if you can comfortably do so. Otherwise, you risk seeming as though you're expecting him to "take care" of you, and apparently, that's not his style.