@everephebe: The one who extends the invitation should expect to pay – whether male or female.
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I agree with what @Bellatrix said. I was with men who were intimidated by my education being more advanced than theirs and one resented (yet took advantage of the fact) that I was earning more than he did. But that was purely their own insecurities in thinking that I was “out of their league”, and that somebody “better” would come along and I’d be gone. That pissed me off, because it meant they had no faith in my feelings for them.
Another factor (which is hopefully fading as society evolves) is based on the traditional masculine role of being the strong one, the provider, and dominant force within the family unit. This sense of being the ‘alpha’ is what I think makes some men homophobic, as well—the idea of being “someone’s bitch”—whether male or female—again plays into insecurities. And the more “macho”, or paternalistic, a culture these men are from, the greater a problem they have with this concept; as many have never had to deal with the concept of being the “inferior” or the “minority” figure in any aspect of society.
A person who knows and is confident in who they are and where they are in life can handle being with a person who has perhaps gone further in one area or another of their life.
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It’s not totally relevant to this question, but as I wrote my comment, I recalled a first-born Irish-American guy I knew who was appalled when the court system unfairly showed inequality toward him as the father in a custodial situation. I said, “Welcome to the real world, blue-eyed golden child.” The idea of not being given preference was foreign to him.