Blog
A simple script for asking for money back
I once rewrote the same text message nine times before sending it. Not a breakup text. A text asking my friend Hannah for the $45 she owed me for concert tickets. Nine drafts, for forty-five dollars.
I don’t think I’m unusual here. Asking for money back is one of those tiny social tasks that feels way bigger than it is, mostly because we’re scared of sounding cheap or accusatory. So we either don’t ask at all, or we ask in a weird, overly apologetic way that makes the other person feel worse than if we’d just said it plainly.
What I’ve landed on, after a lot of trial and error and a few cringey sends, is that the words matter less than the tone, and the tone mostly comes down to a couple of things. Be specific about the amount and what it was for. And don’t sound mad, even if you’re a little mad.
That’s basically the whole script. But how it sounds changes a lot depending on who’s on the other end.
The people you text every day
With close friends, lighter is better. You already have a rhythm with them, so match it. If you normally trade memes and voice notes, a stiff “Hi Hannah, I wanted to follow up regarding…” is going to land like a letter from your landlord.
For Hannah, the version I finally sent was roughly “hey! venmo me the $45 for the tickets whenever you get a sec, still thinking about that encore.” Two lines, one of them not about money at all. She paid within the hour.
The trick with friends, I think, is that you’re reminding, not collecting. Most of the time they just forgot. Treat it that way and they’ll probably be relieved you said something.
Family, which is its own weather system
Family is trickier because there’s history baked into every dollar. A brother who’s borrowed before, or a parent who’d be mortified to be reminded. You often need a softer opening and a little more warmth before you get to the number.
When my brother owed me $200 from helping cover a moving truck, I didn’t text. I called him instead, and after we’d talked about his kids for a while I said something like, “Oh hey, while I’ve got you, I’m squaring up my month and I’ve still got the $200 for the truck on my list. Whenever works.” He said “oh man, yes, totally forgot,” and that was the end of it.
Mentioning that you’re tidying up your own finances is a nice move with family. It makes it about your bookkeeping instead of their failure. My mom used to do a version of this with a notebook in the kitchen drawer, and it still works decades later.
Coworkers and the in-between people
Then there’s everyone else. The coworker who borrowed $20 for lunch, or the old roommate you don’t really talk to anymore. These are the ones where it’s easiest to let it slide, and also the ones you’ll stew about the longest.
With people you’re not close to, I’d go a little more polite and a little more complete, since they won’t have the context in their head. Something like this:
Hi Jordan, hope the new job’s going well! Just a quick note that I still have you down for $60 from the group dinner at Luca’s in March. Venmo or Zelle is great, whatever’s easiest. Thanks!
It’s specific without sounding like an invoice, and it gives them an easy way to pay without a back-and-forth. I’d leave off any deadline. Deadlines with acquaintances tend to read as passive-aggressive even when you don’t mean them that way.
If you’re stuck on wording entirely, there are tools that’ll draft it for you now. OweMate can write a polite reminder on iPhones with Apple Intelligence, friendlier or more formal depending on who it’s for, which is honestly not a bad starting point if you’re a nine-drafts person like me. You can always tweak it before you hit send.
A couple of things I’d avoid no matter who it is. Opening with “Sorry to bother you” makes it sound like you’re doing something wrong, and you’re not. “I hate to ask, but…” does the same thing. Just ask. Nicely.
And if you don’t hear back, one follow-up is totally fair. People get busy, and phones eat messages. Keep the second nudge as light as the first, and then let it breathe for a bit.
Hannah, by the way, now sends me the occasional “venmo me whenever” text when it’s her turn to front the tickets. I like to think I taught her that. She’d tell you she taught me.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.