I lent a couple hundred dollars or so to a friend, basically for his share of our apartment’s deposit. Our other roommate, who was also living with me at the dorm at the time, did the same.
We had a falling out a few months later (sadly, before we had moved into the new place – it was a college town, and you lined up your place to live by March or so for fall). Long story short, he became a pompous ass who would frequently tell us how stupid we were and how brilliant he was, while he would come by and drink our alcohol and hang out in our room. We were talking about pranks and practical jokes for some reason, and he said “I’ve never been pranked or misled in any way. I’m simply too smart for that.” Yeah, whatever. So we lived in the same dorm and I slipped my key onto his keyring, and took his – my roommate agreed to let me in.
Well, we got rather drunk and he wandered off to his room after I had fallen asleep, and it was unlocked, so he didn’t find out about the key until it stopped working the next day. He thought his key was broken so he paid the dorm to retool his lock, which was, IIRC, about $50.
When I found out, I copped to it and immediately offered to pay him the $50. My roommate, being in on it, said she’d chip in and we could either pay him cash (if he needed it now) or he could take it out of what he owed us. I really did feel very bad about it, and I’m still kind of ashamed that I did it. He was a douche, but it was a stupid joke at best.
However, he decided for some reason that the joke was some kind of hate crime (???) and told us that we were vile and terrible human beings. Further, because his time was so valuable as a pre-med student (with no job, so double ???) and it had taken about an hour, that he was keeping all the money we had lent him (about $500 total). He then didn’t talk to us until we all moved in together, which as you can imagine was delightful, but of course we were locked into a lease.
I tried to make peace but he wouldn’t have any of it, and he was generally a big problem for that whole year, but whatever. I can’t stay angry that long, but I guess he could. But I never forgot that money.
Now for a certified genius he was pretty stupid from time to time. He had worked out that the company (due to previous problems) will just split the payment three ways between three tenants to pay back the deposit, which he made it clear he was going to keep. However, he he put all the bills into his name when we moved in because we were too stupid to do it or whatever. So I worked out that if I didn’t pay him for the last month’s bills, plus one bill of the previous month, I’d pretty much have it covered within a few bucks. So the second-to-last month I “forgot” to pay that bill. And the last month, we had moved out, and I sent him a letter that he could take the bills out of the money he owed me. Clear conscience, all was set right with the world. (Mr. Genius agitated awhile about suing me, which I said he could, since I still had evidence of the loan – but he never did, and convinced his parents to pay it for him. And kept the deposit. What a guy.)
Now my other roommate never forgot either, and did the same thing. But she also had a friend in Barcelona and she talked with her a LOT during that last month. Quite a very lot, to the tune of several hundred dollars. And she made it very clear that as he had taken money from her in poor faith, she was doing it too, and to go fuck himself. Now normally I would have really opposed this, and I obviously didn’t do the same thing, but he was a bigger asshole than I can really put in words, so I figured, whatever. He really did deserve that, and way more.
Anyway, so I got my money back but I learned a good lesson. When you think someone is kind of a prick and vicious to other people but he’s witty and amusing and nice to you, watch yourself. I truly believe he was a sociopath, based on all that I’ve read, and once we crossed him the thin veneer of friendship melted away.