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"I (30F) have been best friends with Callie (29F) since 2016, and I consider her to be more like a sister. Callie has always been bad at managing money. Any time we go on trips, I pay for everything, and she usually takes weeks, sometimes months, to pay me back for expenses. I’m usually fine with this because I trust her and know she would never not pay me back. A few years ago, we both moved to bigger cities and assumed we were going to be making better money. We made a dumb decision to invest in something that basically ended up having no value. A few months afterward, Callie told me flat out she was not going to be able to keep up with the monthly payments. I am actually making more money in my city and am good with finances. Since I can handle it better financially, we came to an agreement that she would pay the $2k yearly taxes and I would cover the monthly payments of $500. We decided we would split the initial down payment ($2k each) and then figure out the rest once everything was paid off. All in all, she probably owes me upwards of $18-20k if you include interest. This was in 2023, and needless to say, the whole thing has put a strain on our friendship. While she’s managed to keep up with the taxes each year, she did not start paying me back the $2k for the down payment until a couple of months ago. I’ve been extremely patient with her, but I finally had to talk to her about a payment plan that was more concrete than just her saying she’ll “send me what she can when she can.” The last time I visited was for another friend's 30th birthday party, for which we were allowed a plus one, so I brought Callie. She drank too much and got upset over nothing, completely out of the blue; I ended up having to babysit, and it snowballed into a huge fight between us. We resolved it, but the stress of it all is definitely causing us to have these rifts more often, and we don’t stay in touch as much as we used to. This past weekend, I flew into her city for an event that we both attended. She started asking me about my birthday plans, since it’s coming up in a couple of weeks. I usually like to do a big party or trip, but I decided to keep it low-key this year and was telling her. She started saying she still could fly in just to spend the day and do something, since she’s pretty much always been there for me, at which point I said that I would rather have her pay me back first than spend money coming to visit. I honestly feel bad for feeling how I do, but it’s been so long that she owes me money, and while I don’t expect her to be a hermit and do nothing but be a slave to her job, it also sucks to know she is out spending money when she could be paying me back instead. Personally, if I were in debt to a friend, I would be working and putting as much as I could toward that until it was entirely paid off, but I know everyone is different, so AITJ?" Another User Comments: "Perhaps no one told you... But there is no such thing as lending money to family or close friends. You give them money that you're okay with never receiving back. Money breaks relationships. ESH. You're not wrong for wanting your money; however, this is your mistake. And honestly, you're not a great friend but an enabler. You knew she was poor at managing her finances, yet still, you took her on trips and paid for her, only to want her to pay you back. Why are you inviting her on trips she clearly can't afford or manage with her poor financial decisions??? You even invested with her... Does that even make sense to you? I doubt you will get your money back. This relationship was doomed to crumble as soon as you started counting up receipts" Midsummer_nights Another User Comments: "Pretty soon, she's going to pick a huge fight with you that will effectively end your friendship. That way, she doesn't have to feel guilty about not paying you back, because you're the bad guy. I've seen it happen time and again. NTJ but you were pretty dumb. Consider this an expensive life lesson." LissaBryan Another User Comments: "ESH. Honestly, if you knew she was bad with money, I’m shocked that you decided to go in on an investment like that with her. It also sounds like the investment was shady to begin with (not illegal, just financially risky), so… At this point, I think it’s time to simply cut your losses. Stick to the payment plan you agreed on and that should be the end of the story." Far_Quantity_6133
