What to do when a friend owes you money

I'm frustrated. I've been frustrated for a few months about this subject, so it's time I write about it. The vast majority of what I write for myself ends up being only for myself because it's way too personal to post, but I think this one will be more cathartic if I know feel strongly enough about it to post.

Back in May, I was at Exxxotica Miami, which was a pretty good fan show. I had a nice time, and as I previously blogged about, I made friends with Lexi Love, who turned out to be a really cool girl. On the night of Stormy Daniels' big party, around 10pm as I was getting ready to head out, I got an IM from a friend (we'll call him Scott) back in LA. He told me that one of our mutual friends (lets call him Dan) had been put in jail that night. I informed my friend that Dan was no longer a friend of mine because we fought too much. He said he was fairly aware of that, and if he didn't feel it was necessary, he wouldn't have contacted me to ask for help.

Scott said that he had tried several times to send bail money by wire to Dan's brother, but that it wasn't working. He told me that if I would try and was able to send money that night, he would pay me back the next day by going to his bank. He just didn't want Dan to have to sit in jail more time than was necessary. I knew Scott was good for the money, and I trust him. But as I was crying, I let him know that I just desperately needed to keep Dan out of my life, and so I was sorry but I just couldn't bring myself to get involved.

I walked away from the computer and continued to get ready, determined to not let Dan's problem ruin my night. But the more I tried to ignore it, the more I kept crying. Dan has an incredible knack for taking a situation where everyone knows that he's the instigator, and making people wonder if they're judging him too harshly.  So there I was in Miami, crying in my hotel room, makeup ruined, doubting myself and knowing that I wasn't going to be able to enjoy myself that night.

So I got back on the computer, and told Scott that I was going to help Dan. Because I was the bigger person, and because i was doing it as a personal favor to Scott. I spent over an hour trying to wire money to Dan's brother. It didn't work.

Unfortunately, it served as a catalyst for Dan and I to start talking again. We went back to our old pattern of getting along for a tiny bit, and then him purposely pissing me off just to see how far he could push me. Then I'd get upset and tell him to go away, and he says "but you're so special to me". And I feel like an ass. And it goes on and on.

About a week or so after Miami, Dan told me he needed to pay back his brother, because his brother was having problems paying bills. He said that if I loaned him some money, he'd pay back his brother, and then pay me back within 2 weeks. Before the two weeks was even up, he extended that to 5 weeks. Then at 5 weeks, it became 2 months. It's now been over 4 months.

About a month ago, after having asked him a few times to PLEASE send me a check, and repeatedly being told that the check would go in the mail the very next day, I told him that I was feeling taken advantage of. He told me that he had been going to send me the money, but that something else came up, and he needed the money for that. And that had happened a couple of times in a row. I firmly told him that I had loaned him the money so he could pay back the bail money to his brother - NOT to help him out of every future financial whatever that would come up.

So here's my situation...  Dan has gone back to acting like an asshole and is currently not talking to me. And in a way, I'm thrilled. It's what I was happy with back in May. So now I'm trying to come to terms with the possiblity that perhaps it's worth just chalking that loan up as a loss. Because I don't want to talk to Dan again. And if to get the money back, I'd have to keep him in my life even marginally, I'm better off without it.

-September 24, 2008