A few years ago, I wrote about how to lend money to friends without letting it ruin the friendship. To quickly recap, a friend needed help paying the rent. She had never asked me for money in all the years we’d been friends, so I knew she had to be in a pretty desperate situation. In fact, she was even on medical leave and tried to return to work early, but her doctor (and therefore her employer) refused to sign off on it.

So although I normally think that lending money to friends is a bad idea, this seemed different. I loaned her the money. Although she promised to pay me back, I looked at the loan as a gift, and expected that I would not be repaid. It would have been nice to be repaid, but I was being realistic based on all of the stories I’ve heard about lending money to friends. Therefore, I was only willing to lend what I was willing to lose. I also helped her boyfriend get a job.

My friend never did repay me, which was fine because I’d already assumed that I would not be repaid. Her boyfriend took the job offer and promptly lost the job. (She told me that the boss expected her boyfriend to “just do whatever he was told to do.” Um, yes, that’s how most jobs work, especially when you have next-to-no experience.)

So that whole situation was a one-time thing, over and done. But in the last year or two, someone else I know started hitting me up for money. Money for rent, money to put minutes on his phone. In these situations, I still think my original stance is best, which I wrote about before:

“I don’t believe in loaning money most of the time. It’s not that I don’t want to help make things better, I just think that in most situations it’s a temporary fix. If someone can’t make a house payment this month, what’s going to change next month? In many cases, money troubles are a sign of ongoing issues and habits.”

So I’ve not loaned him any money. But the thing is, so far I’ve made excuses about why I couldn’t loan him money. I dance around the question because I feel like a jerk for saying no, for saying that I’m tired of feeling used (even though I’m not loaning him any money).

Logically, I know that he’s the one who’s being a jerk and trying to take advantage of his friends, but emotionally, it’s not that easy. When he tells me that he sent out resumes but is worried that employers won’t be able to call him because he doesn’t have a lot of minutes on his phone, I feel bad about not helping him. Even though frankly, I don’t even believe his stories and reasons anymore.

He’s also hit up all of his other friends with similar requests. Some of them avoid him now. One mutual friend suspects drug use. Another friend has cut ties by defriending him on Facebook and bluntly saying, “I have my own bills to pay.”

But I have yet to do that. Maybe I don’t want to seem mean, or maybe I’m avoiding confrontation. Maybe I feel bad for him that his life has turned out like this. I’m not sure why it’s so hard for me to be blunt, even when he is trying to take advantage of me.

So readers, if you were me, what would you say to someone who constantly hits you up for money? What if they are someone you were once close to and still care about?


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