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Hello all, I recently got into a bit of a dilemma with a person who I thought was a friend. As the title says, this is going to be a little long, so brace yourselves. For the better part of a year, I've been working with some wonderful people, and although our job doesn't pay a livable wage, we still had a pretty good time. I managed to make a few friends, including one young woman person whom I considered a best friend (since I don't have many close friends). The young woman whom I became close friends with has two children, and oftentimes, she needs additional money to take care of them. The father of her children is not very active in her children's lives—and in many cases, is antagonistic towards her. From what I'm led to believe, they've been in physical altercations, for example. Naturally, I wanted to help her out, so I gave her money from time to time, and didn't worry about her paying it back. The exception to this rule would be two times when she asked me for over $100. My personal rule is that if anyone asks me for $100+, I make them sign a contract stating that they will pay me back within a certain time or face the possibility of legal action. The first time, she paid me back no problem. The second time ... Over the last couple months, I find out that my friend was pregnant again. The father is the same guy who's not reliable and antagonistic towards her. She tells me that she needs money for the abortion, which I gave to her (though not without having her sign a contract first). Shortly after that, she loses her job, so naturally, I tell her not to worry about paying me back since I know she wouldn't be able to afford to. Instead, I ask her to be my wingwoman, since I have a hard time meeting and connecting with women, so having her introduce me to women and accompany me when I'm ready to meet women in social settings would help. However, I find out through one of my other friends that she's pregnant again by the same man. At first, I just think she made a bad decision. But there's more: from what I'm led to believe, she never terminated her pregnancy. She used the money I gave her for something else. When I found this out, I was overcome with rage and grief stemming from dishonesty and betrayal. Here's the thing though, the contract states that she had to use that money for its intended purpose, and if she doesn't, I can take legal action. But should I? On one hand, I want that money back, but on the other, I just want to wash my hands of the whole thing and refrain from speaking to her again. Thanks for reading this long, drama-filled post.