One of my former students followed me on Facebook, so I follow her too. I taught her in high school, and she is 25 now, out of college, and from what I can tell of her posts, really struggling with money. She is a waitress and most of her posts are complaints about money, her job, etc.

I find her very attractive. I have plenty of money to spare. I’m trying to think of polite ways to proposition her. I would pay her a week’s waitressing salary for a single night with me. But how does someone even go about asking?