Sugar Baby relationship
There's a waitress at the bar I frequent that I have gotten very close to over the past couple months. In that time period, at times it's been slow in the restaurant, we've talked about more personal things. A couple weeks ago, she was really upset one day and told me that her ex-boyfriend broke into her apartment and stole all the cash she had stored in her hiding spot and that she was going to have to pick up extra shifts and beg her landlord to give her a couple extra days. I said to her, "let me help and when you come up with the money, pay me back." I had the amount she needed in my car, I went and got it and told her I trust her to pay it back. three weeks later, on the date she said, she paid me everything plus one dollar as a joke. I took her for some drinks that night after her shift and told her my plan. I said, "Listen, we've gotten close over the past couple months so I hope this doesn't upset you but I have an idea that will work for both of us. I am too busy/don't feel like dating right now and you need to make more money than you're currently making if you're going to make your dream of going back to school a reality. Why don't we help each other out? She smiled at me and said, "I like you a lot, and trust you, but let me think about it." I said,
"that's fair, not trying to upset you. I just think it can be mutually beneficial." We changed subjects and drank some beers before leaving. Two days later, she texted me and said, "Ok, I'm in." I replied, "sounds good. This will be fun." Since then, I've helped her with her bills, budgeting, a new apartment and she's going to start taking classes this summer too. She's helped me with all of my needs too. She's been very helpful and courteous. I love the arrangement and I really think she does too.
I sometimes fantasize about having a sugar daddy relationship with my best friend's college aged daughter.