I cant believe that any sane male would agree to pay more just because he makes more money. They are not married, it is a completely different situation if they were, but this is not a good way to get things started. If she makes only 1000$ per month, tell her to stop being a mooch and get a real job and/or an education. Ill gladly pay for the bulk of drinks and dinner for a girl Im seeing, but anything like this is split 50/50.