"he doesn't like women who can't pay their own way" He has issues with money and women. I enjoy taking care of my girlfriend and paying her way. It's not like she is a spoiled Paris Hilton type that leaches off of me and you definitely don't seem like the type either.
It seems that your self worth has become identified with your dollar amount after dating him. Before it wasn't a problem but now it is.
I suggest finding someone new. It's never a good sign when you have to 'work things out.' That is a sign that the relationship is flawed but you are forcing it to work when it clearly doesn't.
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