The Must-Knows of Modern Reimbursement Etiquette

By Lauren Malanga

Whatever happened to the golden age of etiquette books? Back when Emily Post was practically a household authority and Brooks Brothers casually stocked How to Be a Lady next to the navy blazers. For those of us who endured multiple seasons of Cotillion and live for the art of a perfectly wrapped hostess gift, the lack of modern etiquette guidance hasn’t just been noticed — it’s felt like a gaping hole in the social fabric.

Here’s the thing: talking about etiquette today is really talking about the slow fade of tradition. The rituals that once offered comfort and connection — holiday dinners, handwritten thank-you notes, RSVPs that meant something — are increasingly edged out by the chaos of life. Work deadlines bleed into weekends, holiday plans get ghosted, and somewhere along the way, creating your own rules became the new rebellion.

But let’s get to the point. If we’re redefining etiquette for the modern era, we need to start with a platform that definitely didn’t make it into your grandmother’s charm school syllabus: Venmo. Yes, Venmo etiquette is a thing, and ignoring it? That’s a fast track to awkward texts, simmering friendship tensions, and low (or high) key resentment.

1. When Not to Venmo Request

Planning your own birthday dinner? You chose the restaurant, crafted the guest list, and sent the invite — you do not Venmo request your guests after the fact. The only exception? If you’ve been upfront from the start. Something like: “I’d love to celebrate my 25th at Sant Ambroeus! It’ll be around $75 per person — totally get it if that’s not in the cards; feel free to join us for drinks after!” Transparency is chic — and spares everyone the post-dinner awkwardness.

Now, if your friends are collaborating on the plans, tossing out restaurant ideas, and actively involved in the celebration blueprint, that’s different. They’re considering their wallets when offering suggestions, which means a Venmo request won’t feel like a blindsiding move.

2. When to Use (and Avoid) the Dreaded “REMIND”

The passive-aggressive Venmo reminder button? Proceed with caution. It’s the digital equivalent of an “are you forgetting something?”. Before hitting that REMIND button, try sending a casual text or — wild idea — actually calling your friend. Life happens, and most of the time, a gentle nudge feels way more subtle than a notification that screams you owe me.

In a world where ghosting isn’t just for dating apps, maybe bringing back a little modern-day etiquette isn’t the worst idea.

3. The “Round-Up Rule”

If you’re splitting the bill and someone’s already fronted the full amount (especially if they covered the tip), round up when you Venmo them back. It’s an easy way to acknowledge their effort — plus, adding a couple of dollars for their trouble is the ultimate classy move. Small gestures go a long way in the etiquette department.

4. Keep Your Transactions Private — Unless It’s a Joke

We get it, public Venmo feeds can be weirdly entertaining, and a means of social media snooping. But unless your payment comes with an inside joke worth sharing, default to private. No one needs to see your $7 coffee transfer — or your entire social circle’s financial play-by-play.

5. Pay Promptly — It’s 2025, Not the Stone Age

If someone covers you for dinner, drinks, or that overpriced Uber you “forgot” about, pay them back within 24 hours — or preferably while still in the car or at the restaurant. While I may not be pro-reminder button, no one should have to chase you down. Delayed payments scream disorganized and — worse — disrespectful. It’s digital, it’s easy, and your reputation will thank you.

6. No Nickel-and-Diming

Sending a Venmo request for $3.75 from that group dinner? Absolutely not. If the difference isn’t enough to cover a cup of coffee, let it go. Hyper-precise requests feel petty and can leave a bad taste— especially when you’re splitting with close friends. Round it down and keep things gracious.

In a world where common courtesy can feel like a dying art, maybe starting with Venmo isn’t such a small thing after all. Because nothing says I’ve got my life together like paying your friends back on time — with style and a side of good manners.

Lauren Malanga is a master of people-watching and over-analyzing, crafting thought-provoking content with a sharp, witty edge. A LA native turned NYC resident, this freelance writer and former branded content editor has an eye for details. Follow her on Instagram @laurenmalanga for a glimpse into her unique perspective.