I agree - the whole situation is not ideal and quite complicated. Also there is a difference between some kind of sexual adventure, even if both of them are single, and a serious, commited relationship that would lead to a stable family and kids, happy ending and stuff.
Of course, a married guy is a different story completely.
I think some women may feel very opposed to the social cliche of a strong, powerful, guy in a tuxedo (James Bond, typically) who seduces an attractive woman who has a lesser position. Old fashioned people love this scenario - take Pretty Woman, where he has the power and money and she needs the "job". I think a modern woman might hate this kind of cliche and expect the man she likes to find someone on the same level or even higher.