Stop Using Venmo Like a Broke Jerk—A Guide
Top 10 rules for the p2p age
Venmoing your friends for small, exact amounts is broke jerk behavior. Studies find the more precise your payment, the more petty you seem. And according to user surveys, venmoing under $5 is rude. You may think you’re being fair, but you come off as cold and transactional.
In part 1, I argued venmoing small amounts is a cope. We want to offload the guilt we’ve internalized about owing money by paying our friends back right away. But we don’t need performative financial hygiene to prove we’re reliable. In fact, the very opposite is true. We need small debts between friends to build trust.
That said, Venmo isn’t all bad. I believe we can co-opt this trust-corroding technology and use it in ways that incentivize connection over transaction.
So when to use Venmo and when not to? And how to use it in a prosocial way? Here are the new rules and the social science behind why they work.
When NOT TO use Venmo
#1 Do not surprise request
A surprise Venmo charge can kill a friendship. In part one, I mentioned a woman who received a $6 request for a glass of wine she had at a friend’s house, and another who was charged for ingredients after attending a dinner party. The audacity is next level because the consequences are seemingly less costly. But where you save on confrontation, you lose on trust. An unexpected Venmo request feels like a betrayal, because it’s a violation of the social contract. What you thought was a gift of hospitality suddenly has a price tag.
A 2024 Cash App survey of 1,000 users found that 73% of people have had at least one major negative experience due to cost-sharing with friends. We too often use peer-to-peer (p2p) apps to avoid confrontation (see #2), and financial ambiguity breeds resentment. The cure for this is expectation setting. It's simple and non-negotiable. If you expect repayment, say so before you pay.
Some scripts to try:
Set the expectation: “I’ll grab this—can you Venmo me after?”
State the amount and ask for opt-in: “Should we get the $30 appetizer platter? That would be $10 each. Does that work for everyone?”
If it’s your treat, make that clear too: “I got this! Don’t venmo me.”
#2 Do not avoid confrontation
Difficult conversations are fundamental to building and deepening relationships. Friends who can engage in constructive conflict have higher mutual trust and more durable relationships. “Whoever owes you money may have a reason they’re waiting to pay you back,” advises The Cut, “give them a chance to explain before you robo-remind them.”
If you think a friend is ignoring your Venmo request, you must address it directly. This is uncomfortable, yes, but a passive-aggressive Venmo reminder won’t resolve the issue. Text them, call them, or bring it up next time you see them, “Hey, can you get me back for that hotel soon?” Or, more directly, “I really need that money for the hotel by Friday.”
Setting a precedent really matters. The ability to have a direct, honest conversation about money is a sign of maturity and respect. It reinforces the idea that your friendship is more valuable than the debt owed.
#3 Do not venmo small tabs
Small, informal debts play a crucial role in trust building. If you, like me, have a habit of performative venmoing to offset the discomfort of owing people money, it’s worth reconsidering this impulse.
Studies on trust formation show that it’s built incrementally through predictability, reliability, and generosity. Crucially, trust can’t develop unless you have opportunities to exhibit these traits. Routine acts of generosity create low-stakes moments to build trust: one person extends a small favor without immediately tallying and settling the debt.
“This was implicit interpersonal logic in a pre-Venmo age,” writes Luke Winkie in Slate, “now it’s been rendered into a radical act.”
Instead of venmoing for small expenses, try initiating a cycle of reciprocity. Phrases to try:
“Let me get this round, you grab the next.”
“It’s my shout.”
“Let’s make this a regular thing! You can get me next time.”
I recognize that if you venmo small tabs back and forth, the net result might be financially identical to trading shouts. But the psychological effect is very different. Explicitly settling every minor expense frames the interaction as a transaction rather than an act of trust. Less vigilance over small debts signals confidence in the relationship itself.
In Hate Read, “Nicola Dime” (a great pseudonym), argues in favor of splitting the bill evenly rather than itemizing, “We don’t split the bill because we think we all ate the same number of bites of branzino. We split the bill because this meal is an investment in our friendship—a sign of trust that we’ll do this again and again and therefore, over time, everything will even out.” (more on this in #5 below)
When TO use Venmo
#4 Do give Venmo gifts
You can venmo someone for no reason. It’s very fun. Small, thoughtful, and surprising Venmo payments are a real joy—something p2p technology enables that cash never could. A $5 “latte on me” or a “get yourself some bubble gum” message is so much more valuable than the money itself. This is great for long-distance friendships or, in San Francisco, your Berkeley friends.
In Catherine LeClaire’s WIRED article “How to Use Venmo for Good,” a friend sends her $0.25 with a note “get yourself a temporary tattoo”. In response, she embarks on a quest across Brooklyn to find a vending machine with the perfect prize.
“Most of us don’t need the charity. We could buy ourselves the latte or gum,” LeClaire writes. “What we need[…]is for someone else to remind us of the things that make us happy, and gently insist we take the time to experience those things.”
The key here is that a Venmo gift must be a surprise treat for when you can’t be there in person. (If you’re in-person, see #3). In a time before Venmo, you might send a singing telegram or a bouquet of flowers (you can still do this). But a surprise Venmo gives them the choice of when/where/how they redeem the little treat on their own terms.
#5 Do itemize the bill
For many p2p app users, splitting the bill evenly is no longer the norm. The 2024 Cash App survey found that 43% of Gen Z agree that “dividing the dinner bill when one party ordered significantly more items is not ok” and 39% agree calculating exact bills for a restaurant or bar tab is proper.
Plus, restaurants and servers are sick of the hassle. It’s increasingly common to see “no split checks for parties greater than 4” printed explicitly on the menu. This is where Venmo shines. Using p2p apps to split the restaurant bill is this tech’s best use case.
Even so, a few rules apply for bill splitting politely:
1 card pays, Venmo immediately.
One person in your party puts down their credit card. Pass the itemized bill around, tally up what you owe, and venmo the cardholder. Trust your friends to do the math discreetly without making a spectacle. Best practice is to send the money to the cardholder before leaving the table (see #6). Want the credit card points? Then you must have the fastest wallet draw when the bill comes.
Shared plates, shared bill.
Although splitting evenly is no longer the norm, if your friend group loves small plates and shared bottles, an even split is fair. Again, just set the expectation before the bill comes. Something like, “Everything on the menu looks amazing, want to order three entrees and split them?”
An important exception for generational and wealth divides
Millennials and older generations, who statistically make more money than Gen Z, do not need to be as budget conscious. If the difference is less than $10 between your orders, consider just splitting the bill evenly.
As Dime writes in Hate Read, if your friends are making six-figure salaries, “there is simply no reason to be nickel-and-dime-ing your loved ones in pursuit of saving $9.”
You really should read her whole rant, but this part hits especially hard: “My gripe here is not with people who have legitimate reasons to watch their dining budget, but with people who do not have those issues and yet still insist on making friendship feel so blatantly transactional at the dinner table.”
#6 Do pay promptly
The life cycle of a venmo is 48 hours. In a 2019 survey of 1,000 Venmo users, 72% agreed that the appropriate window of time to send a Venmo request is within 24 hours of the transaction. Once received, users agreed there’s a maximum of 24 hours to send payment.
If you need more time to pay, text the person you owe and tell me when they can expect reimbursement.
Also, pay in real time when possible. In that same survey, 42% of respondents said if one person picks up the check at a group dinner, you should venmo the person covering the bill before leaving the table. The bigger the amount, the more urgently you should pay the person back for your share.
#7 Do round up or down
Do not send exact change. People who venmo exact amounts are perceived as petty—even if they’re just trying to be precise. Researchers found, “petty behavior can undermine relationships even when [the payment] is objectively generous.” This means giving $5.15 can be worse for your relationship than is giving five dollars even. This effect was consistent across cultures and age groups.
Why is pettiness so harmful? The researchers propose that the attention to trivial detail makes the interaction feel too much like a market-price relationship.
“Between retailers and customers, such ongoing cost-benefit analyses are typical: Payment amounts reflect the quality and quantity of work,” they write. “Between friends, in contrast, cost-benefit analyses are uncommon and even inappropriate.”
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#8 Do gently compete
Competing for the bill is a healthy, happy ritual. The theatrics are important, and they serve a dual purpose:
No one assumes entitlement, and everyone signals a willingness to contribute.
It allows for a graceful negotiation of hierarchy.
This is especially useful when there is a power differential in salary or seniority level. The gentle competition lets those with greater financial means signal generosity without seeming condescending. If you’re a lowbie at dinner with your C-suite friend, you both know she’s got an expense account. It makes sense for her to pay. But it would be impolite to assume! When the bill comes, everyone should reach for their wallet and initiate the friendly argument of “Let me get it” “No, no, let’s split” “No, no I insist.” After one or two protests from the lowbie, it is then considerate to let the higher status person pay.
If you’re with a friend of equal standing, and you have an established rapport of treating each other, a playful contest is still appropriate. “Let me get this one.” “Oh no, you got the last one!” “Can I venmo you?” “No, don’t worry about it. Get me next time.”
If the friend paying the bill wants to treat you, do not send them a Venmo reimbursement. You may think you’re being kind, but you’re actually refusing their gift. This could be interpreted as a rejection, or worse, a desire on your part to sever the social tie.
The key is not who wins the check battle, but that the battle happens at all. The shared performance is an acknowledgment that the reciprocity cycle is in motion.
Anyway, rules 1-8 are all very important, but here are the two that matter most of all…
#9 If you invite, you pay
When it comes to paying the bill—with or without Venmo, no matter your gender or romantic entanglement—there is really only one rule: your invitation, your bill.
There aren’t many exceptions, but there are a few:
If the invitee is significantly wealthier and insists on paying
If a clear precedent or understanding exists
e.g. at family dinners your rich uncle always pays; you’re the executive assistant who organizes the lunch meeting, but the CEO is the true host; you’re the maid of honor organizing a bachelorette trip, but bridesmaids understand they will split expenses
If your invitation explicitly signals that they should pay
Saying “Let’s get sushi on Friday” implies you’ll cover it. Saying “You should take me out for sushi on Friday” shifts the expectation.
For those in the dating scene, consider this cruder variation: “If you penetrate, you pay”. Use whichever variant applies best to your life I guess? If you’re curious how this intersects with chivalry and gender roles, I’ve written about that here.
In the 2019 Venmo survey, 63% of users agreed “the person who asks for the date and picks the location is typically the one who should pay the bill (regardless of gender).” Only 30% of respondents thought the bill should be split evenly.
#10 Acknowledge and offer
Second most important rule: if someone else pays, you should offer to venmo them. This is especially important in new relationships where expectations aren’t yet established. The Venmo offer is the new social calibration: it signals awareness of the financial exchange and sets a precedent for future outings.
At a restaurant, if the bill comes and you’ve gotten a more expensive entree or cocktail, acknowledge it and offer to pay the difference or cover the tip. Mary H. K. Choi writes, “Just offer! Admit that you ordered a whole-ass brook trout more than me on the check! It’s all I ask.”
The point isn’t perfect financial parity. It’s about demonstrating awareness and respect, so that generosity feels mutual rather than one-sided.
We’re nearing the finale of Season 3 of The Ick. Stay tuned for the final installment next week!
The social rulebook has been rewritten in our post-pandemic world—and it's left us wondering, “Am I doing this right?” Season 3 of The Ick is creating a modern field guide to social etiquette and decoding the hidden architecture of human connection. Subscribe here. Find season 1: embarrassing stories here, and season 2: the five senses here.
Further reading:
There’s simply no reason to be nickel-and-dime-ing your loved ones in pursuit of saving $9, “Nicola Dime” on Hate Read (2025)
Gen Z Money Manners Report, Cash App (2024)
194 Modern Etiquette Rules for Life After COVID, The Cut (2023)
A guide to Venmo etiquette, PayPal (2019)
Pettiness in Social Exchange, Kim, Zhang, and Norton (2018)