For millennials, Venmo is an emotional wrecking ball

Emily is a successful 24-year-old, working in finance with lots of dating opportunities. So when she was recently asked out by an acquaintance to grab drinks and he insisted on paying the bill she wasn’t surprised.

It was what came next that surprised her. A couple of days later, Emily received “a notification” through a payment app called Venmo that she owed him $23 for her share of the bill.

Emily wasn’t sure what happened—did she give off vibes that she didn’t want a second date? Or maybe he wasn't into her, so the feeling was mutual.

Either way, isn't there a better way to get blown off than getting charged on Venmo?

“I feel like he got the benefit of taking me on a date without paying for it; he got to look like a gentleman without the cost of chivalry,” she said, requesting that we don’t use her full name. “Getting a Venmo request later from someone who insisted on paying taints the relationship.”

Emily eventually paid the guy his $23, the cost of her Martini, and vowed never to look at him again.

As a millennial (I’m 24), I can attest that this is not an isolated incident. It’s no secret that those in the millennial generation (people born between 1981 and 1996), and Generation Z (people born between 1997 and 2012) are addicted to technology. and social media in a way our parents never were. It’s the benefit and the curse of being born when we were. Stuff like Venmo makes life easier—and we love anything that makes getting through the day easier.

The flip-side is that it also makes our lives less fulfilling. We interact less and avoid confrontation. In the "olden days," say pre 2000, if you wanted to date someone, you had to have a conversation “IRL,” Millennial speak for “In Real Life.” You didn’t just rely on Tinder, Hinge, Bumble, and “The League,” (for those who graduated from Ivy League schools or want to associate with those who did), to meet someone. You asked them out on a date, face-to-face.

It was all about trial and error, and it worked, at least better than its working now. My friends and I constantly complain about the superficiality of various relationships. Maybe we should look inward and realize its our reliance on technology that is making it more difficult for us to lead a fuller life.

Venmo Upending Relationships Over Money

Venmo has taken the debilitating effects of the social media addiction to a new level, I believe, because my generation has now grown accustomed to avoiding in-person conversations about one of the most important issues facing people and relationships: Money.

If you can’t have honest discussions about money, how do you really get to know someone? The fact that money is such a complex, hot-button issue makes it all the more important to deal with in-person, rather than through some app.

Of course, I’m not the first person to point out how social media is changing all types of human interactions, Venmo included. But the other critiques of Venmo seem to miss the bigger issue as they focus on fatuous subjects like anxiety over being left out of the latest girls trip because you can see what your friends are spending money on (one of the many "useful" features of the Venmo app).

What I’m concerned about is something more important than that millennial anxiety-related disorder known as FOMO or “Fear of Missing Out.”  My worry is the escapism that Venmo leads to is creating a generation of lightweights, afraid to argue about money, or just about anything else.

I’ll be the first to say that my generation receives a lot of unwarranted criticism from Gen-Xers and of course Baby Boomers for being narcissistic whiners when in fact we are the ones serving in the military, and they were the ones who created the financial crisis and slumbering economy that came after. But what they have on us is that they have learned to address problems and conflicts in person, which is a critical part of being an adult. Our confrontations too often take place through various apps in a virtual world. We don’t naturally confront in person. When we do argue, much of it is done through text messages. We don’t break up in person; we send instant messages.

And when we think we're owed money, we Venmo.


Wendy Dickinson, a behavioral psychologist says the research on Venmo, and social media in general, is pretty clear: It has made my generation less capable of dealing with problems and relationships because these devices “eliminate the amount of vulnerability and connections people have in real life. Instead of having to face difficult conversations and work through issues about financial boundaries and values in person, people are decreasing their connectedness with each other.”

Her solution? “We need to start to have conversations that feel messy, ask how people feel about things, and lean into the connection,” Dickinson said. “That’s how you develop intimacy in relationships. Venmo isn’t the problem; it’s a tool. The problem is how we use the tools available to us.”

I hate to pick on Venmo because it is a such great tool. You simply download the app and anyone with a U.S. bank account who has done the same can transfer money to you and vice versa. It's convenient—instead of splitting the dinner bill six ways, one person picks up the tab and then charges the others.

It's effective, which is the biggest reason everyone I know is on it. You can just ignore the Venmo request, but most people I know say they don’t. The reason: being “Venmoed” is not just annoying, but there is a certain stigma placed on the recipient, and that stigma usually leads to the desired result. If you don’t pay the request, or take too long to do so, you’re somehow reneging on a deal. You’re a cheat even if you really aren't as was the case of Emily and others I will soon point out.

So, in the end, most people just pay.

And that’s why Venmo is a great business. The app became available in 2009 in the wake of the financial crisis and the onset of the Great Recession as unemployment grew, wages stagnated and job prospects particularly for millennials looked bleak. People like me just out of college and working at low paying jobs needed to pool resources to have fun.

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The company’s parent is PayPal, another highly successful money transfer system designed to eliminate the need for money orders and checks, which has some high profile backers such as tech billionaires Peter Thiel, Reid Hoffman, and Elon Musk. Venmo itself was founded by Andrew Kortina and Iqram Magdon-Ismail, two millennials who met in college and created the app a few years after graduation.

It looks like they’ve hit it big again; $19 billion in payments flowed through Venmo in the fourth quarter of 2018, an 80 percent increase from the same period last year, according to PayPal’s fourth quarter results. One major reason for Venmo’s success is that these guys certainly knew their target market. Nearly 75 percent of Venmo's users are under the age of 35 and these guys know most of us don’t earn million dollar salaries trading for hedge funds, or writing code at tech firms. Between college debt, stagnating wages, and the cost of drinking LaCroix seltzer water, millennials and Gen Yers simply don’t have a lot of money to throw around.

Venmo makes our conspicuous consumption a little easier to finance.

OK it’s a great product, but there’s a human cost to all that money flowing into the pockets of billionaires as I also recently discovered.

Not too long ago I went to one of those high-end coffee shops with someone who was once a close friend. I ordered what’s known as “a matcha latte with oat milk,” which was a little more expensive than a Starbucks Venti, but wasn't breaking anyone’s wallet.

After an hour of catching up, I explained to my friend I had to run to the doctor. She offered to pick up the tab, which I thought was considerate, but reasonable since I’d hosted her for dinner several times in the past.

As I was in my Uber, something weird happened: I received a notification on my iPhone from her labeled “VENMO” with a seemingly innocuous emoji for green tea.

I was “Venmoed” $7.58, a number so specific it felt offensive.

Friends suggested I send her a Venmo request of my own, for the cost of the food I’d made her, which was significantly more than $7.58. It was tempting, but I decided to take the high road (well kinda), indulge my inner millennial (and not confront her directly), and do some reporting on the millennial Venmo phenomenon.

Venmo Horror Stories

That’s when the horror stories started piling up.

What was interesting is that all the stories—mine included—followed a similar pattern of millennials passively aggressively requesting money. Relationships ruined. And at the center of it all was this app. Here are just a few:

  • My brother's best friend, let’s call him Andrew, 25, doesn’t want us to use his real name because of business reasons, was moving to San Francisco and needed a place to crash for one night.  Andrew’s friend offered up his couch, supposedly free of charge that is until about a month later, when Andrew got a Venmo bill for $500. He paid, but the friendship will never be the same.
  • My friend Becca, 24, is not afraid of letting us use her real first name because she is still steaming over her Venmo nightmare. Last year she lived in a small apartment in New York City with three other young women, and got Venmoed her share of the electricity bill. When the charges began appearing exceptionally high, she asked the roommate who handles expenses for a copy of the bill. “She just yelled at me and stormed off,” Becca said. In the end, Becca had a choice: Pay the bill or find another apartment. She decided to suck it up and keep paying, but suffice to say, they’re no longer friends.

Like any good reporter, I asked a Venmo spokeswoman to respond to the issues I'm addressing in this piece. In a statement to FOX Business, she said: “Venmo is loved by millions of users for its simplicity and ease-of-use that helps to remove the awkwardness of dealing with cash and IOUs between friends. This commitment and passion has truly helped us reshape the way people send and receive money. As Venmo grows, and the money transfer landscape evolves, we believe Venmo will continue to provide users with resoundingly positive experiences.”

I'm sorry, these are not resoundingly positive experiences. Granted, Venmo is a great product and an amazing business, but again, I want to refer to what life was like back in the olden days when my parents were dating. There was no Venmo; they had to figure out bills and split dinner checks in person. That’s one of the reasons why they got married; they grew comfortable dealing with some of the most difficult issues facing couples. They did it face-to-face through trial and error and it worked. They’re still married over 30 years after they split their first meal.


Dickinson believes Venmo is such a successful business not because millennials are destitute, but because it capitalizes on our obsession with avoiding confrontation —and that this is the root cause of our generation’s problem in developing real, long-lasting relationships.

"At the baseline this is not just about money: this is a cultural choice for millennials, and millennials value things that are efficient, easy, and smooth," she said, "Technology checks a lot of those boxes, but relationships just don’t work like that.”

Perhaps, Jean-Paul Sartre got it wrong. Perhaps hell isn’t just other people, but rather, other people requesting $2.75 from you.