>>81153882>rich bitch turned friend turned loverI know I wouldn't.
It is sort of weird imagining though, catching the eye of a girl way WAY out of your social and economic class. You have so many stories about the rich man falling for the common girl, but the rich girl following for a common boy's rarer. Sure there's the whole pool boy and the rich dilettante scandal mess, but that's not really what this would be.
Does that even happen? It's got to be strange for a guy, dating a girl who has far more wealth than you. What would you even get them, what could you even do for a date? Everything you make or do could probably be done a hundred times better with her money and connections. It's got to be intimidating, wondering what she would see in you.