Background: LTR (28F) worked at a restaurant as a server. Older man (70s) comes in with his son, tips LTR $50 on a $70 check. Days later, older man comes back to restaurant has different server but tells server to give my LTR $100. She thanks him and he offers her his business card, and says "give me a call if you ever want to do something else". We find out that he is a multi-millionaire (possibly a billionaire). She ends up calling him and giving him her resume (she has a good resume), but nothing comes of it, because she finds a position with another company.

Current situation: Several weeks later, LTR has started a new sales position. As an effort to reach her goal for the month she reaches out to the wealthy man who I've mentioned. He says he'd love to help her out but does not want to come into her office (as she requests). He instead suggests they meet for lunch. She agrees to meet him then calls me after the lunch.

She calls me immediately because she is overwhelmed by the lunch. She tells me that he basically expressed 0 interest in her product but would like to "invest in [her]". He tells her that he will invest $20k in her over the next few months. She can choose how to spend the money. She counters with a suggestion that he instead hire her and put the money toward her salary. He tells her that is something they could discuss in the future (basically acknowledging that he doesn't want to discourage her from quitting her new job so soon - one way to look at it). Basically the conversation ends with the understanding that she will be receiving a check from him at the end of the month that will cover a portion of the "investment".

The problems I'm seeing with this are: - What is he getting in return? What does he expect in return? - How can she actually put the money toward her goal if the purchases need to be made directly through her company - not through a check that he has made directly out to her. - It's obviously super sketchy

I'm aware that he baited her with his interactions at her restaurant job. Also, one could say that he is just a generous guy who's trying to help out a girl in need. How am I suppose to feel about this though? Can I really hold it against her for accepting the help? We spoke about it before and she made it clear that she wanted to be a team about this. What do you guys think about all this?