Here's how to navigate the treacherous waters of Venmo requests without losing all your friends
In Reader’s Digest’s new series, “Is It Really Rude to…,” Charlotte Hilton Andersen tackles low-stakes etiquette questions from everyday life using a combination of her common sense and vast knowledge from writing 50-plus etiquette stories for this site. Have a situation you can’t stop ruminating on? Email us at [email protected].
My friend Anna and I have a standing coffee date each week where we meet at the gym cafe post-workout. She always gets a black coffee, I get a protein shake, and we catch up on life because we just get each other so well. I mean that emotionally, sure, but also—I thought—financially.
Boy was I wrong.
Here’s what happened: Anna was running late, so I did what any good friend would do—I ordered her regular drink so it would be ready when she arrived. Very thoughtful of me, right? Then, while sitting there basking in my Friend of the Year glow, I opened Venmo and sent her a request for $3.75. I even added a coffee emoji because I’m not a monster. She paid it immediately without comment, but later that week, another friend mentioned how Anna had told her about my “coffee bill” in a tone that suggested I’d invoiced her for breathing my air. Apparently, buying someone’s coffee and then Venmo requesting them makes them feel less like a cherished friend and more like Account Receivable #47 in your small business ledger.
My actions made sense to me in the moment. Anna is a wealthy CEO. I’m a freelance writer and mom of five who considers it a good day when I find a 20 in my coat pocket. Half the reason we meet at the gym cafe instead of her preferred bougie coffee spot is because I can’t afford $10 lattes that come with a chakra guide. (The other half is my employee discount, which is the only reason her coffee was $3.75 instead of $6.) In all the months we’ve been meeting, she’s always bought her own drink, and she’s never once covered mine. She knows I’m broke AF, so in my mind, I wasn’t being cheap, I was just … keeping things balanced?
But clearly they were all talking about me. I spent the next three days spiraling: Was I The Cheap Friend? Was this a gift or a loan? Do friends keep receipts? Should I have just eaten the $3.75 (IN THIS ECONOMY?!) and then let it slowly build up resentment until I “forgot” her birthday?
This isn’t just a me problem. More and more of us are navigating this exact minefield of modern friendship finance, and even a few bucks feels high stakes when $3 coffee is considered a bargain and paying rent requires creative accounting and possibly a side hustle selling plasma. Whether it’s coffee, splitting an appetizer, feeding someone’s parking meter, or buying concert tickets in advance (which now cost more than my first car), the question looms: Do you Venmo request for reimbursement, or do you swallow the cost and add it to your mental spreadsheet titled “Times I’ve Been Generous (That Will Definitely Come Up in Therapy)”?
Friend math didn’t used to be this complicated. You either paid for someone or you didn’t. If you covered a friend’s coffee, it was understood as either a treat OR they’d physically hand you cash on the spot. Now we have all of these different payment apps. The technology has outpaced the etiquette, and we’re all just out here guessing about the right thing to do.
What is the proper etiquette around Venmo requests?
Obviously, I can see the case for requesting. Money is money, and $3.75 is still real dollars even if it’ll barely buy you a side of avocado these days. Some people genuinely prefer the clarity of immediate settlement—you bought something, they pay you back, everyone’s even, no weird “who owes who” mental accounting six months later when you’re trying to remember if they covered your movie ticket in March.
But the more I sat with it (and by “sat with it” I mean “obsessively ruminated about it at 2 a.m.”), the more I understood Anna’s point. Sending a Venmo request for a $3 coffee makes you look petty. Like, hilariously petty. “I bought you a small cappuccino and I need immediate reimbursement” energy is not typically the vibe people are going for in their friendships. Not to mention that the mental load of you requesting, them seeing the notification, opening the app, confirming their payment method and sending you $3.75 probably costs more in collective time and emotional bandwidth than the coffee did.
What do the unofficial polls say?
When I polled my social media followers, the responses were decisive. About 60% said Venmo requesting for anything under $10 is tacky unless it was explicitly discussed upfront (“Hey, I’m in line, what do you want? Just Venmo me.”). Another 35% said it depends on the relationship and financial situation. And a bold 5% said they request for everything, including the dollar someone owes them for splitting a pack of gum. So we’re all confused—got it.
The missing piece in all of this, I think, is communication. Most of this awkwardness evaporates if you just talk about money beforehand. But it seems like talking about money feels more taboo than talking about sex these days. Truly, my friends will spill every detail about their last hookup over brunch but won’t give the tiniest glimpse into their bank account. Other than collectively complaining about the increasing cost of existing, we don’t really talk about money. Which leads to gray areas: Did they ask you to grab them something with the implication they’d pay you back? Or did you offer as a nice gesture and then surprise them with a bill? Are you both broke 20-somethings eating ramen for dinner, or established adults with retirement accounts? Is this your best friend of 20 years or someone you’ve hung out with twice? Has the relationship generally felt reciprocal, or are you always the one covering things?
But the real question is, what does this request cost beyond the $3? If it’s going to make things awkward in a lovely friendship, then that coffee just became a very expensive social experiment.
The verdict: Generally rude, unless explicitly agreed upon beforehand. If someone asks you to grab them a coffee and says “just Venmo request me,” then absolutely do it—they’ve set the expectation. But if you offer to grab someone a coffee, order something for a friend who’s running late or cover a small spontaneous purchase, sending a Venmo request afterward transforms your “generous gesture” into an ambush invoice. (Anna, if you’re reading this: I’m so sorry. Next coffee’s on me. For real this time.)
For amounts under $10 with friends, family or regular social contacts, the proper etiquette move is to either cover it as a gift or explicitly establish the transaction upfront. “I’m grabbing coffee—want anything? Just Venmo me” is clear. Buying someone a coffee and then billing them is chaos.
The actually rude moves? Venmo requesting someone for something you offered to “treat” them to, requesting it days or weeks later (was this a gift or not?!) or making someone feel cheap for questioning a request. And on the flip side, consistently letting people cover you without ever reciprocating makes you a mooch, which is equally bad.
So here’s my new rule, learned the embarrassing way: When in doubt, eat the cost of small things. If it’s going to bother you, don’t buy it in the first place. And if you do need to request money back, establish that before you’re standing at the register. “Want me to grab you something? I can add it to my order and you can just Venmo me” is totally fine. Surprise-billing your friends for their morning coffee? That’s how you end up drinking alone.
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