GIF: Jim Cooke (Gizmodo)

Venmo is an app that should be simple and transactional. Instead, it’s thorny and oftentimes awkward to navigate. It’s truly wild that a self-professed “digital wallet” stirs up so much drama.

“A guy I was cheating on my boyfriend with once Venmoed me the morning after we got drinks, when I’d told my boyfriend I was with a different friend,” one friend told me. “This could have been avoided if he made the transaction private, or if all Venmo payments were private. It’s hard for me to understand what the advantage is of having them be public in the first place.”

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This specific scenario was certainly a problem attributed to Venmo’s default public setting which one must “opt-out” of, but it also signals some astonishing naïveté by the sender who didn’t check to see that their shady transaction was private. While there’s a lot left to be desired with regards to the features and settings of the app (not to mention that whole privacy thing), there are also issues when it comes to how people are using the app. What are you people doing? Why?!

Below you will find an etiquette guide that I very scientifically compiled by asking friends, family, and colleagues what Venmo habits irritated them most, and then consulting an emotionally intelligent user (me) on best practices to adopt to address and evade them.

The content of your payment or request

The app requires you include a description for each payment. That’s bad user experience, but it’s also the catalyst for the first issue: don’t be a dick about captions.

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“Your vague and mysterious emojis are neither mysterious nor vague. Please stop narcing with trees and snowflakes,” a coworker suggested.

Being incriminating isn’t cute. What’s more, by continuing to treat the app like it’s a social network—trying to come up with the most creative or intimate description—you are just perpetuating the pressure on others to overshare and expend mental energy on coming up with the coolest way to convey that your friend spotted you a beer at the bar while Venmo (probably) gleans your data. The solution to this is simple: keep it simple. Did you pay someone back for lunch? How about the caption “lunch.”

Full disclosure: I have dicked around on Venmo. I once sent my roommate the entire lyrics of Yellow Card’s Ocean Avenue because his girlfriend admitted to never having heard the song. I also once sent a friend a series of one cent transactions, spelling out a love note, to her utter irritation. And I also once tried to send a friend the entire Wikipedia plot of Annihilation to charge him for a movie ticket. (It went over the character limit). I think sparingly being an asshole on the app is low-key acceptable. But keep it at a minimum, guys.

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How long you should wait to request money

Here’s a common scenario: you’re out with a friend. The bar has a minimum, so you spot them a drink to meet it. “Thanks, dude, I’ll Venmo you for that.” But you’re out, you’re having a nice time, and it doesn’t feel natural for either of you to whip out your phones and send a payment or request in that moment. At what point is it acceptable to send that person a request for the drink? You don’t want to be That Guy, sending a request in the same breath that your friend says they will pay you back. Too soon, and you might come off rude, distrustful. But wait too long, and maybe your friend forgets (or “forgets”).

I think waiting 12 to 48 hours is acceptable. If you’re out for drinks on a Thursday night, for example, I think it’s totally fine to send that person a request the next morning. If you want to wait, give them the space to remember to pay you back themselves, wait it out until Saturday night.

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This situation is a bit more nuanced when it comes to shared costs among roommates. Venmo has become a common tool to split bills and costs for household items, like paper towels and toilet paper. For those payments, it’s acceptable to send a request to your roommates right when you make the purchase. However, people appreciate a message from their roommate or partner before they get the request as a heads-up. “Otherwise it would feel like I was getting a bill from my own housemates,” a friend said.

And none of this addresses petty and inexplicable Venmo requests. A colleague pointed out that an ex-roommate would send her charges for household items that she didn’t even use. For example, you may think it’s nice to get flowers or donuts for the apartment, but if you didn’t consult with your roommates before making those purchases, then you bought those out of the goodness of your heart. Don’t charge them, even if they reap joy from the contribution. Without consultation, that’s a gift, baby.

How long is acceptable to wait until you pay someone back

When it comes to paying someone back, you should do it as soon as you are financially capable. That might be in that moment, the next morning, the next week, or maybe even the next month. This one requires some emotional intelligence and communication. Is your friend tight on money? Don’t be forgetful or lazy. Did your friend spot you because you’re tight on money? Make sure they have a sense of the deal they’re making in that moment. “I can pay you back when I get my paycheck next week,” or “Can I pay for two month’s of utilities next month?” Be transparent—don’t swindle your friends.

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It gets even more complicated when you are splitting the check among a larger group of people. I once attended a bachelorette party where eight women wanted to split a bill among… eight cards. One brave woman instead suggested that one or two people split the bill—something that I acknowledge requires some privilege, depending on how much the bill costs—and the rest Venmo them. In those instances, when someone is footing a hefty cost, you should send them the money you owe within the hour. Don’t make them keep track of who has and hasn’t paid them back, and don’t make them stretch themselves thin only to have you send them back your portion of the bill a few days later. If everyone thinks like that, that’s a supremely shitty spot for that person to be in.

That being said, one of the most common complaints is that Venmo doesn’t have a great feature to automatically remind people to pay you back. You can manually go in and send someone one reminder if they haven’t paid you back in a timely fashion, but it puts the onus on lender to remind them, and who wants to do that?

If you’re still defaulted to public, wyd???

Despite Venmo’s “opt-out” default, you can still easily change your settings to private or just between friends. We are not starved for platforms that afford us the option to show off what we’re doing, who we are hanging out with, where we’ve been, and what we’re eating.

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Spontaneous acts of generosity

It’s undeniable that Venmo makes paying people back a hell of a lot easier than about a decade ago. But it also has evolved random acts of generosity, both for the good and the disappointing.

“I hate the capitalism aspect,” a colleague said. “A thing that’s nice about friends is you take turns treating each other to things. Having to keep a tally and commodify every hangout is bullshit.”

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“It’s expected that people just split everything now,” another friend said. “There is no treating someone or taking them out to dinner/coffee. We’re of the mindset that it all evens out at some point, but now I have to keep track of what I paid vs. what others paid.”

It’s an unsurprising and unfortunate side effect of convenience—but that doesn’t mean you can’t also use the app to spread unsolicited kindness. I’ve used Venmo to send friends money for a drink or a sweet treat on their birthday if I can’t celebrate in person. I had a friend send me a small amount of money to treat myself to a coffee and a pastry after a breakup. I’ve also had friends “pay” each other compliments, sending tiny payments with a nice caption. I recognize that this contradicts my early etiquette rule—to not treat the platform like a social network.

I still agree that it should largely be used in an emotionless and transactional way. But I also think it’s okay to rarely make exceptions—especially if it is to thoughtfully (and privately) make your friends day a little better.

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