Venmo-Stalking Is the Best Stalking. But What Does it Tell Us About Ourselves?

venmo stalking cat

Think about the most perfect couple you know. For the sake of this article, let’s call them Mike and Julia. (Common white millennials, y’know?)  Maybe they’re the two people from your freshman year floor who hit it off immediately and have somehow only grown stronger together. On Instagram, they post gorgeous, aspirational photos of their summer weekends in East Hampton and winter ski trips to Vail. Their engagement—on Nantucket, duh—was something out of a Martha Stewart fever dream, and their Boston apartment is perfectly decorated via Restoration Hardware. Their dog, naturally, is a yellow lab named Charlie. They seem like the ideal match. Two people seemingly built for one another—destined for a nondenominational wedding followed by a country club reception featuring a crab cake bar and a signature cocktail (made with gin, never vodka). 

Then, you check your Venmo account. You were only there to request $40 from your best friend for drinks last night. But the second you open the app, you’re met with a confounding discovery: Julia has charged Mike for a beer. Aren’t they engaged? you think. Intrigued, you click over into Julia’s account. Ninety percent of the posts are seemingly insignificant charges between her and her partner of nine years. There’s rent, sure, but there are also charges for toilet paper and pizza and batteries. Has the perfect couple fallen from grace? Is there something sinister lurking beneath the veneer of breezy selfies and Breton tees? Maybe, but maybe not.

As a reminder (or for anybody still using *shudder* cash), Venmo launched in 2009, as way for regular people to seamlessly transfer funds up to $5,000 between each other. When you first log in, you securely connect to your bank account, from which you can easily move money any time you want to pay somebody. The app was acquired by PayPal in 2013 for $800 million, and reportedly has 65 million users to date.

It’s convenient, sure, but the most interesting byproduct of the app’s rise is the social one. When you open it, you’re met with a timeline similar to what you’d see on Facebook or Twitter. For each entry, you see “Person A paid Person B,” followed by a description of what the payment was for. Some transactions are self-explanatory, while others, often communicated via emoji, require a little more sleuthing to figure out. During a quick scroll of my own Venmo feed, I saw a bunch of rent payments, some split Ubers, a vet visit for someone’s dog and a payment for Megan Thee Stallion tickets—pretty standard stuff.

Still, there are gossip-y diamonds in the rough. “Honestly, Venmo is way more real than, like, Instagram,” says Katie, 30, a teacher from Washington, D.C. “On Instagram, it feels like everyone is ‘performing’ for their friends and followers. On Venmo, though, you can’t fake it. Everything is laid out on the table.” 

It’s a fair point. In a world where most social media posts are meticulously staged and edited, the authenticity of Venmo is refreshing. Yep. Todd and Brendan went bowling. Then they got burritos. And Todd paid for all of it. And to that end, following your friends and acquaintances on Venmo is a tiny way to understand the weird relationship we have with money—how we share it and how we spend it. Would Mike and Julia ever advertise having separate bank accounts, and nickel and diming each other for paper products? Probably not. But on Venmo, it’s all out in the open. 

Stalking on the app does have its limitations, of course. First, users are able to hide their transactions. (Luckily, “public” is the default setting, meaning many people—yours truly, included—are too lazy to switch to private.) The second limitation is that you’re never able to see how much money is being exchanged—just that it’s being passed from one party to another. It’s still not enough to dissuade people from snooping. Becca, 35, a marketing specialist from New York City, admits, “Even though you can’t see the specific amounts people are sending to one another, it’s definitely interesting to see who’s traveling all over the country every weekend. I have no idea how much anyone I work with makes, but it’s sometimes wild to see the things they’re dropping money on on Venmo.” 

Ally, 29, works in finance in New York and has raised her eyebrows at some of her coworker’s money habits. Having started out as the lowest level junior analyst possible, she’s well aware of how much her younger colleagues are making right off the bat. That doesn’t stop some of them, she’s noticed, from living like a character in The Wolf of Wall Street. “It really makes you wonder how much money certain people come from,” she muses. “If you’re going to Michelin-starred restaurants on the regular, I have to consider how much generational wealth is going on in your family.”

Some would argue this kind of speculation is gauche. Others might call it empowering to move closer to a world where it’s not weird to know what the people around us make or how they spend their earnings.  

Financials aside, Venmo stalking also speaks to our insatiable love of gossip. I spoke to one woman who, rather harmlessly, discovered that two of her coworkers were dating on the DL because of frequent late-night Venmo charges. Katie, the teacher in D.C., has a slightly more salacious story. After copiously following a former college-mate over the past few years, she and her friends surmised that the woman might have a sugar daddy. “No judgement, do what you’ve gotta do, but when I see an older man (based on his picture) sending money to a woman in her early 30s with the caption ‘just because,’ it sounds some alarms.” (We won’t get into the logistics of a ‘[leaf emoji]’ purchase, but we will say Venmo isn’t always used for legal transactions…)

But where there’s gossip and giggles, hurt feelings can’t be far behind and, indeed, many people I spoke to for this story reported a heightened sense of FOMO after trolling Venmo. I’m reminded of the time, pre-COVID, when I turned down a weekend trip to upstate New York with a handful of my friends. I don't need to spend the money, I reasoned with myself. I've been to the Catskills a dozen times. Then, the weekend arrived and I was confronted, via Venmo, with everything I was missing. There were back and forth charges for the gorgeous Airbnb; the Insta-worthy apple orchard; the dinner at a chic bistro helmed by, what else, a Brooklyn transplant. Had I been invited on the trip? Yes. Still, with every transaction I saw, I regretted my decision more and more. 

Does Julia ever feel that same FOMO when she Venmo-watches her single friends living it up in Vegas? Probably. Have you ever felt crummy having to see that several of your pals are out without you, all splitting pitchers of beers and late-night cheese fries? I'm going to bet that you do. Because, while Venmo stalking is pure voyeurism, it's also--like any social media platform--a way to showcase the parts of our lives which once were private, albeit with a bit less veneer and a bit less curation.

In other words, if you're worried about optics, don't invoice for the toilet paper.

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sarah stiefvater

Wellness Director

Sarah Stiefvater is PureWow's Wellness Director. She's been at PureWow for ten years, and in that time has written and edited stories across all categories, but currently focuses...