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I lent my friend $400 last year and here's what I'd do differently
I lent my friend Marcus $400 last February, and he paid back the last of it the week before Thanksgiving. Nobody got hurt, and we’re still friends. I’d call it a success, sort of, the way you’d call a road trip a success when the car made it home but the AC died somewhere in Arizona.
He texted me on a Tuesday night. His car needed new brakes, and the shop wanted the money before they’d hand back the keys. Payday was nine days out. He asked if I could cover it “for like a week or two,” and I sent it on Venmo before I’d even finished reading the message. Marcus is the guy who helped me carry a sleeper sofa up four flights of stairs in July. Of course I said yes.
A week or two turned into a month. He paid me $100 in March with a thumbs-up emoji. After that, nothing until June, when $50 showed up out of nowhere. The rest trickled in over the fall in a couple of bigger chunks. I never once asked him for it directly, which, looking back, is probably the part I’d change first.
What actually bugged me
It wasn’t really the money. I didn’t need that $400 for rent, and I think if I had, I’d have handled the whole thing very differently. What bugged me was the fog. I didn’t know if he remembered. I didn’t know if he thought “a week or two” was a real promise or just a nice thing people say. Every time he posted a photo from a concert or a brewery, a small, petty voice in my head started doing math it had no business doing.
And I hated that voice. It made me feel like a worse friend than the guy who owed me money.
Marcus, for the record, wasn’t dodging me. When we finally talked about it over beers in October, he said he’d felt bad about it the whole time and figured I’d say something if it was a problem. I’d figured he’d say something if there was a delay. So we both just sat there, separately, being polite at each other for eight months.
What I’d do differently
The biggest thing is so boring it’s almost embarrassing. I’d say the plan out loud. Not a contract, nothing weird, just one more text after the Venmo went through. Something like “no rush at all, just let me know roughly when you think you can swing it back.” That one sentence would’ve turned a vague promise into an actual shared understanding, and I think it would’ve let both of us relax a little.
I’d also decide, before hitting send, whether I was lending or giving. Those are really different things, and I blurred them. If I’d thought of it as a gift that might come back, I wouldn’t have spent the summer quietly keeping score. If I’d thought of it as a loan, I would’ve felt fine checking in. Instead I treated it like a loan in my head and a gift in my behavior, which is roughly the worst combo available.
Then there’s the check-in itself. I waited way too long. A light, friendly mention around the one-month mark would’ve been totally normal, and it probably would’ve saved Marcus some guilt too. People who owe money usually know they owe money. A kind nudge gives them an easy opening instead of leaving them to wonder whether you’re secretly furious.
And I’d write it down somewhere. I genuinely lost track of whether the June payment was $50 or $75. When he sent the last chunk, I had to scroll back through months of Venmo history to confirm we were actually square, which felt a little like checking someone’s homework. A note on my phone with dates and amounts would’ve taken maybe thirty seconds each time.
The one thing I wouldn’t change is saying yes. He needed the help and I could afford it. He also paid back every dollar, which counts for a lot. I’m not walking away from this thinking you should never lend to friends. It’s more that if you’re going to do a nice thing, it’s worth spending five extra minutes setting it up so the nice thing stays nice.
The part I keep thinking about
I’m not sure money between friends ever gets fully un-awkward. Something about it brings out a weird mix of pride and guilt in basically everyone, me included. But I’ve noticed that most of the awkwardness lives in the stuff nobody says. Once Marcus and I actually talked about it, the whole thing deflated in about ten minutes. He apologized for the slow trickle. I apologized for being strange and quiet about it. Then he picked up the next round, which I’ve decided to count as interest.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.