Conventional wisdom says that you shouldn’t loan money to friends… but anyone who tells you that has clearly never tried to book an AirBnb for eight people who live in different states, or asked a waiter to split a bill five ways. At some point or another, you or your friends will owe each other money. Ideally, this will be resolved quickly: you will send a Venmo request, they will accept, life will go on. But of course, that won’t always be the case. In instances where things are more complicated, here’s how to handle it.
Follow up about the money they owe first, assuming good intentions.
If someone has owed you money for two months, it’s easy to get very worked up about what a bad friend they are. But so often, the person has just forgotten about the situation entirely, and would be mortified to know you were stressed about bringing it up to them.
So give them the benefit of the doubt and approach them with an open, neutral tone. If the socially acceptable padding of a few days has gone by when you make this ask, giving them a firm deadline a few days out is a nice thing to do. So you could say, “Hey, I’m not sure if you saw my Venmo request from Monday for the Airbnb, but would you mind accepting that?”
Call out the fact that it’s becoming A Thing.
If you’ve already asked a few times and they’ve definitely not forgotten about it, you don’t need to take them at their word when they swear that they’ll pay you back tomorrow. It’s totally reasonable to ask them what their deal is.
What to say:
“I hate to keep bugging you about this, but I really need to be paid back for the drinks from last month. I’m not sure what’s going on, but can you just Venmo me right now?” (A good option if the conversation is happening in person.)
“Hey, when we talked the other day, you said you’d pay me back on Friday. We’ve been going back and forth about this for weeks now… what’s going on?”
Ideally, the person will be honest with you about what is going on—maybe they got hit with some unexpected expenses, or a check they were waiting for didn’t arrive—and you can figure out a plan for them to pay you back.
If they continue to be cagey about it or blow you off, you’re absolutely justified in continuing to bug them about it. It’s extremely OK to want your money back! If someone tries to dodge your request with a shamey, “It’s just $20, chill,” you can say something like, “If it’s just $20, then why won’t you give it back?” You don’t have to drop the subject to keep the peace (or ever loan them money ever again).
If you don’t agree on who owes what, be direct, but keep an open mind.
There are a surprising amount of gray areas when it comes to money owed within friendships. (Look at r/AmItheAsshole, where a lot of questions deal with money *maybe* owed.) Maybe a friend spilled wine all over your couch and you want them to pay to have it cleaned, or they decided to go over the agreed-upon budget when booking something and you don’t want to pay them.
Cases like these can be tricky, but if you approach them in good faith—firm, but still open and cautious—you’re more likely to get what you want (or at least get closer to what you want). Here’s what to say in some of those moments.
If your friend ruined something of yours:
“I know you didn’t mean to drop pasta all over my top when you borrowed it, but it’s currently unwearable and I was hoping you could [pay for the dry cleaning/pay to replace it/pay half of the cost of replacing it]. Thoughts?”
If your friend went way over your agreed-upon budget when booking something:
“Hey, we agreed on $75 max for these tickets, not $125. I really wish you’d asked me before you’d bought the more expensive ones, because I would have said I wasn’t OK with that. I’m going to Venmo you for the $75 we agreed on, but I’m really not cool with paying the extra. Does that make sense?”
If your friend borrowed something of yours ages ago and still hasn’t returned it:
“Hey, I know I’ve been asking about getting my leather jacket back from you for a while now, and at this point, I’m sort of assuming something happened to it and you didn’t want to tell me. If that’s the case, I’d really like to replace it sooner rather than later; is it cool if I Venmo request you for the $150?”
If you told a friend “Oh, you don’t have to pay me!” when you agreed to do them a favor and you now… regret that decision:
“Is it too late to take you up on your offer to pay me for [dog-sitting/photography job/helping you move]? I know I said it was no big deal when we first talked about it, but I’m realizing now that it’ll be more [time/energy/complicated/expensive] than I had initially thought, and it actually would be really helpful if you were willing to offset those costs.”
If they simply disagree, you’ll have to decide whether it’s worth pushing the issue, if there’s a way to compromise, or if you’re OK with just taking the L. You might decide that $25 or $50 isn’t worth a big to-do with a close friend… but if it’s an acquaintance who stiffed you, or $1,000 is at stake, that might be an entirely different story. If it’s part of a bigger pattern of inconsiderate behavior, or they are being particularly thoughtless, it’s absolutely OK to be upset or frustrated, and to not let it go immediately.
If things go badly, use the experience as data for the next time.
Never saying anything is the stuff long-simmering resentments are made of. Having meaningful friendships and living in a society means occasionally pushing through your feelings of, Ugh, I don’t WANNA, and doing things that really suck in the moment.
If they react badly or you discover you’re on wildly different pages when it comes to money stuff, that’s still very good information to have! It’s good to recognize that this friend who you adore in a lot of ways is not a person who you want to book an Airbnb with or lend your clothes to ever again.
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This article originally appeared on VICE US.