People who are wealthy use their wealth. But for some men, that kind of banter is more confusing than fun. And so the vulnerability produces a number of things that make him even more vulnerable. He is much more likely to crack a joke that has some sexuality in it because he's feeling insecure and he wants to test the waters to see if she is responsive to him. The woman, he says may play along, even if she feels uncomfortable, for fear of alienating him.
Women know it.
They test it. If you have an advantage you shouldn't be allowed to use it. In offices a decade or so ago, women often adopted a much more somber business demeanor, and that style hasn't changed much as they have climbed the corporate ladder. Older women don't use charm as much. They probably just use pure brains and their position of authority or whatever.