And then there's the side that would feel bad about taking her money and it didn't work out.
Uh, John? That whooshing sound you hear? Is that the air rushing past your ears as you fall off a cliff? I'm deliberately taking your sentence out of context to make a point. This sounds a lot like my definition of prostitution (or in your case would that be gigolo-ness?) Is THAT what your radar is sensing is behind her offer?