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Why we're so weird about asking for money back
I once let a coworker keep $60 of mine because asking for it felt worse than losing it.
It was concert tickets. Kevin and I sat a few desks apart and liked the same band. When tickets went on sale he was stuck in a meeting, so I bought two seats. He said “I’ll get you back.” He was a nice guy and definitely not broke. I’m almost positive he just forgot. I never brought it up. Then he took a job in Denver, and that was that.
I’ve thought about that $60 way more than it deserves. Not because I miss the money, but because I can’t fully explain why I didn’t say anything. It would’ve taken one sentence. I’d sent harder messages to my landlord.
The more I talk to people about this, the more it seems like almost everyone has their own Kevin. Lending feels generous and easy. Asking for it back feels like walking into a room and turning the lights on during a movie. So I’ve been trying to figure out what’s actually going on there.
My best guess is that a lot of it comes down to looking petty. Nobody wants to be the person who tracks every dollar. We’ve all met someone who splits the check down to the appetizer they didn’t eat, and nobody wants to become that guy. So we overcorrect. We’d rather lose $60 than risk being seen as someone who cares about $60, even though most of us, if we’re honest, do care about $60.
There’s also this thing where lending money becomes part of how we see ourselves. I like thinking of myself as generous. When I lend someone money and then ask for it back, part of me feels like I’m taking back the nice gesture, like I’m admitting the generosity came with a receipt. That’s not actually true (a loan was always a loan), but the feeling is real.
Another piece, I think, is that asking can feel like a confession. If I ask for the money, maybe it looks like I need it. Maybe it reveals that I’m tighter on cash than I let on. For a lot of people, especially if you grew up in a family where money was stressful or never discussed, that kind of exposure feels genuinely uncomfortable.
And then there’s the trap I fell into with Kevin, which is waiting for the other person to remember. It’s so tempting. If they’re a good friend, surely they’ll bring it up, right? So you wait. And every week you wait, the ask gets heavier, kind of like a text you forgot to answer. On day one, replying is easy. On day forty, you feel like you need to open with a full apology and a life update. Debts work the same way. A reminder after a week is nothing. A reminder after five months feels like an event.
The weird part is that the other person is usually waiting too. Last year, a friend paid me back a loan over the better part of a year (I wrote about it at the start of the month), and when we finally talked, he said he’d assumed I’d say something if it bothered me. We were both stuck in the same polite silence. Neither of us was the villain. We were just two people who’d decided, separately, that bringing up money was rude.
I don’t think it is rude, though. I think it’s just uncomfortable, which is different. Rude would be bringing it up in front of their date, or posting a passive-aggressive meme about people who don’t pay their debts. A quick, friendly mention with the actual amount isn’t rude. It’s information. Most people seem relieved when you do it, because now they don’t have to wonder whether you remember or whether you’re quietly annoyed.
Something that helps me now is thinking about what I’d want if the roles were flipped. If I owed a friend money and forgot, I’d absolutely want them to tell me. I’d be mortified to find out a year later that they’d been stewing over it. That flip makes it feel less like I’m demanding something and more like I’m doing them a small favor.
It also helps to separate the money from the friendship in my head. Asking for $60 back isn’t a judgment on the person. It doesn’t mean I think they’re a bad friend or a deadbeat. It’s just closing a loop, like returning a borrowed sweater. Nobody thinks you’re petty for wanting your sweater back.
I’m better at it now than I used to be. Not perfect. I still catch myself rehearsing a two-line text like it’s a job interview. But I’ve noticed that the anxiety beforehand is almost always worse than the actual conversation, which tends to go something like “oh my gosh, totally forgot, sending it now.”
Kevin, if you somehow end up reading this from Denver, it’s fine. Mostly.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.