Blog
Small debts, big feelings

Twenty dollars is not a lot of money. I want to say that up front, because I’m about to spend several hundred words on it and I’d like you to know I’m aware of how that looks.
A few months ago a friend of mine, I’ll call her Jess, borrowed $20 for a cab after a concert. Her phone had died and she didn’t have cash, and I was happy to help. She said she’d send it the next day. She didn’t. A week went by. Then three. And I found myself thinking about that twenty more often than I thought about my actual car payment, which is roughly fifteen times larger.
That’s a strange thing to admit. I make decent money. I wasn’t going to miss a meal over it. And yet every time Jess posted a picture from brunch, a little voice in the back of my head went, “Nice mimosa. Where’s my twenty?”
I don’t think I’m unusual here. Almost everyone I know has a version of it. The $15 a coworker never paid back for a group lunch. The $30 a cousin borrowed at a wedding. These amounts are tiny, almost silly. But the feelings attached to them are not.
So what’s going on?
My best guess is that small debts aren’t really about money at all. When someone owes you $2,000, it’s clearly a financial thing. With $20, the money itself doesn’t matter much. What’s left, once you strip the money out, is the gesture. It’s whether the other person remembered. Whether they cared enough to close the loop on something that cost them almost nothing to fix.
That’s why it stings. A forgotten $20 can quietly whisper, “You weren’t important enough to remember.” Which probably isn’t true! Jess was not sitting at home plotting against me. She was busy and distracted, like all of us. But the feeling doesn’t care much about what’s true.
There’s another layer to it, I think. Asking for a small amount back feels disproportionately petty. If someone owes you $500, you have social permission to bring it up. But texting someone about $20 feels like you’re the kind of person who counts sugar packets. So you don’t say anything, and the feeling just sits there with nowhere to go, getting a little bigger and a little sourer each time you think of it. It’s a bit like a tiny splinter, easy to pull out but somehow bugging you all day if you leave it.
What I’ve come to believe is that the amount is almost irrelevant. What’s being asked for, really, is respect. Not in some grand, dramatic sense. Just the basic respect of keeping a small promise.
And that cuts both ways. I’ve definitely been the Jess in someone else’s story. I’m pretty sure I still owe my sister Becca for a coffee from, let’s see, maybe 2019? She’s never mentioned it. But I’d bet good money she remembers.
So, Jess. I did eventually say something. I waited until it came up naturally, when she mentioned she was going to another show, and I said, “Ha, just don’t make me pay for your cab this time. Actually, speaking of, did you ever send that twenty?” She was mortified. She sent it right there at the table, plus a few extra bucks “for interest,” and apologized about four times.
The funny part is that the moment the money hit my account, the whole thing evaporated. I just felt lighter. It was never about the twenty. It was about being able to stop thinking about the twenty.
Since then I’ve gotten weirdly fast at paying people back for small stuff. Someone covers my $6 coffee and I’ve sent it before the barista calls the next name. It’s not virtue, exactly. I just know what it feels like on the other end now, and I’d rather not be anybody’s splinter.
I still haven’t sent Becca that $5, by the way. I’m going to do it right after I hit publish. Probably.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.