1. The guy always pays. If the lady in question insists on paying, agree to get the night over with and then find someone else if you are looking for a wife. Ardent feminism or dickering over who has the better job/most disposable income doesn't indicate a fortuitous match.
2. At 50, you'd better be grateful you found anybody worthwhile to go out with. The world is full of unattached ladies but it can be very difficult to find someone who isn't loaded with resentment against the former husband(s) and men in general. If you find a nice, pleasant lady to go out with, don't be an idiot and insist that this rare find has to pay her way.
Given your lack of reassortment skills, have you considered the monastic life?
Wasn't directing that to you, Nick - that was aimed at the moron writing to Miss Manners..
Two words: The Philippines.