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Photo of me holding something I never actually carry, by Gia Cognata

Confessions of a Venmo Voyeur

The secret satisfaction of watching you spend

Sara Benincasa
Jan 24 · 15 min read

My Venmo membership is one of the most conveniently creepy aspects of my digital life. My profile is set to private, but to my absolute delight, most of you have a public Venmo profile. And I love watching what you do there.

Like most of my so-called microgeneration — that space between Millennials and Gen X known as “Xennials” or, as writer Anna Garvey memborably termed it in 2015, the “Oregon Trail Generation” — I rarely carry paper money. As far as I can tell, the founders at Venmo (now owned by PayPal) did not intend to create a looky-loo’s paradise when they cleverly responded to a problem they perceived among then-twenty-somethings like my friends and I.

Launched in 2009, when I was 28, Venmo was marketed as an easy way for pals to exchange electronic cash at a dinner where it may have been too confusing to split a check 15 ways. But the popular app doesn’t only exist to help drunk liberal arts majors divvy up the price of a giant Tex Mex Tower at TGI Friday’s, or, if one prefers a livelier evening, go halvsies on an eight ball.

It’s a simple way to tip a nail technician off the books. The same goes for most situations in which an independent contractor’s place of business takes a portion of a tip given via credit card. If you don’t like to carry cash but you do like to make sure all of your tip (except for a tiny fee) goes to a hardworking individual, Venmo is a very useful tool.

These days, many of us use Venmo to pay landlords, plumbers, babysitters, even chiropractors or psychiatrists. Some people use it for child support payments. How do I know? Because I watch people do all of these things and more, every single day. I watch my friends, and I watch strangers. And I am not alone in my scintillating hobby.

In “Public Displays of Transaction,” the playwright, author and screenwriter Chiara Atik wrote:

As in so much of her brilliant fiction, Atik’s words ring true. But the date of her essay is July 20, 2014. Nearly seven years later, I marvel at how much of my associates’ private lives I can observe via Venmo. Have people still not caught on to the public nature of their transactions? Do they know, and simply not care? Or — and this is the most tantalizing prospect — do they like being watched?

To try to find out, I read a 2018 article from MarketWatch that detailed a project by coder and privacy researcher Hang Do Thi Duc, who analyzed 207,984,218 public transactions posted on Venmo in 2017. The Berlin-based researched found it extraordinarily easy to figure out details about the lives of several Venmo users.

Recently, I found out that my friend’s ex-wife has started a knitting business. I also found out that an ex and her spouse exchange carefully-labeled Venmo payments nearly every week for such specific items as “paper towels” and “half of grocery order.” I really like this ex (as a friend!) and her spouse seems excellent. I hope to split dinner with them via Venmo once we are allowed to do such things in public again.

Apparently, a 2017 investigation by the Federal Trade Commission found that Venmo was “misleading” users “about the fact that they needed to change two separate privacy settings to make their transactions completely private.” The company settled with the FTC, though I don’t know the details of said agreement. In the above-linked article, Do Thi Duc offered her opinion that the option to change one’s privacy settings should be easier and more obvious to product users.

My own data backs this up. I conducted an unscientific poll of my 96,000 Twitter followers, probably 25% of whom are sexy Russian bots trying to sell lingerie and/or engage in the disruption of the American democratic process. With that in mind, the 961 responses to “Are so many Venmo profiles public because…” went as follows:

  • “Ppl just don’t realize it” — 81%
  • “Ppl want attention” — 17.4%
  • “Ppl want to network” — 1. 6%

Several people weighed in to tell me that they hadn’t realized their profile was public. Others said they don’t care, because they use it for only the most prosaic of transactions. Still others told me about their favorite descriptions on other strangers’ profiles (for the record, my favorite is “diet Moderna vaccine.”) Someone offered that they saw one of their own payments labeled “taint,” and could not remember what it was for. They later followed up and added they’d remembered they’d helped a trans friend pay for bottom surgery, and wished they’d sent more than $5.

Quite a few people mentioned they take delight in hitting the heart on strangers’ transactions, because it’s just so odd. I’ve only done that once, with somebody I knew who was paying for hoagies, and he enjoyed the joke.

In the course of my research for this story, a few strangers figured out my own Venmo name and, to my surprise, sent me a total of $41 (I told one I will donate it to the immigration nonprofit RAICES Texas). One woman said, “I just love Venmo-bombing people!” which I found to be rather sweet.

I have a few actor friends who recently shared that this phenomenon has happened to them, with fans leaving such descriptive notes as “that TV show you did” or “the interview where you said [fill in the blank kind thing].” They were flattered, yet uncomfortable with it, as they don’t need the money and did not solicit it.

One woman online advised me to see if I have any famous people’s Venmo contacts, or if my Venmo “friends” have any famous friends, and to follow the trail to see if I found anything neat. What I discovered was that a wealthy celebrity embroiled in an increasingly insane scandal took a lot of boxing lessons during the second Obama administration. There may be juicier revelations to be discovered, but I didn’t have the energy to investigate further. Besides, I remain happily entranced by the hair salon and taco truck adventures of plebeians like myself. To be an actual celebrity sounds terrifying, doesn’t it?

Finally, I decided to review my own private Venmo transactions.

Let us travel all the way back in time to February of 2016, when my journey with Venmo commences. I’d advise you to buckle up, but where we’re going, we don’t need roads. To the information superhighway!

It appears my first act on Venmo is to send money to a friend to pitch in for my girlfriend’s gift (the one who is now in a marriage that involves very precise Venmo transactions.)

I pay rent on my studio bungalow in Silver Lake via Venmo, something I will continue to do for approximately two and a half years, until I return from New York Comic Con to discover a rat infestation, at which point I move to Eagle Rock to live among a plethora of soon-to-be-divorced sad dads with their first TV staff writer jobs.

Later in 2016, around the time I turn 36, I’m seeing a divorced, non-dad television writer who takes me to Disneyland for a few days. It appears we put the hotel room and food on my credit card, as I see a few payments from him related to Mickey-shaped beignets and other important items. He’s a brilliant writer, and even his Venmo notes are sweet. I half-ass the relationship because of course I do.

Sometime in 2017, I’m in the midst of a rather passionately sexless emotional affair with a married artist, which prompts my entry to therapy. I begin seeing a kind, patient licensed counselor and social worker with whom I can never seem to keep regular appointments. Such notes as “missed session” and “sorry for the late cancellation” are further evidence of my inability to maintain solid, mutually beneficial intimate adult relationships. The counselor keeps her Venmo account private, which is apparently not always the case with my friends’ shrinks. One person tells me she had to explain the privacy setting to her own horrified psychiatrist.

Later in 2017, I win $130 from my brother for making the closest guess to the exact time of his son’s birth. We will do no such baby pool for his second son, who will arrive on January 1 of 2021. That’s second baby energy, for sure.

I buy people food, and people buy food for me. I say I’m going to Joshua Tree, and then I don’t, so I get a partial refund for a jaunt with some girls. I go to the Metropolitan Museum of Art with my friend and her son, where he runs around the Temple of Dendur wearing the most adorable spectacles. She tells me his biological parents were runners in high school, too.

My friend in California, a now-retired adult film star, accepts money from me for something called “doggie love.” It is, in fact, actually for a dog-related medical situation. She’s also a fantastic poet and a funny comedian. If she decides to be a doctor or a lawyer, I will not be surprised. Some people are just like that.

At the height of my drinking, I accept $500 from a showrunner friend who is worried that my bank account is overdrawn (again). I pay him back soon enough. A writer-director friend lends me $1000 one November. In December, I pay it back. I’m sober by that time, but not yet accustomed to observing what (or whom) is coming and going.

The years go on. I get my hair done, a lot. I find it comforting. My grandmother and great-aunt owned a hair salon together, which preceded a very Italian point in their relationship where they didn’t speak for twenty years despite living next door to one another. I take my great-aunt’s side in the dispute, though I don’t know what it’s about. They are both long gone, but I still use the Christmas tree angel my great-aunt made for me in 1983. Last Christmas, I decided I’m always going to keep it out. She made brilliant bowtie cookies and pumpkin pie from scratch, too.

I book a boxing trainer, miss boxing sessions and then give up trying to box. Perhaps this is why I’m not a very wealthy celebrity. It seems one must box. I get a new shrink, one who takes payments on a different financial app. We do well together, this shrink and I. Our steady relationship is over two years old as of this writing, though she’s left Los Angeles permanently for upstate New York, and I’ve left Los Angeles possibly-not-permanently for New Jersey. I enjoy our Zoom sessions very much.

I pay editors for various podcasts, including my current one. A friend hires me to give notes on a script, and I send it back because I realize I can’t focus on anything during 2020. A pandemic rages on. I get my hair cut, sometimes outside, sometimes inside facing an open window or door. We wear masks. It’s still a risk, but less so.

The last thing I pay for on Venmo is a new round of blonde highlights, administered in New York City in early 2021. Hair as therapy, one might say. It’s not always easy to find somebody who knows how to cut curly hair, but the Internet leads me to a genius. I find a stylist in the East Village who is brilliant, funny, and has a small but airy salon that boasts a backyard with a beautiful deck. Her wife is a mason and many of her friends have technical skills, which made the build-out last summer a little less complicated. Turning an abandoned old restaurant into a hair salon in the middle of a pandemic is no small matter, but I am of the highly biased belief that queer women can make anything happen.

She provides pink disposable masks for everyone. She’s done haircuts out there for people who don’t feel comfortable staying indoors. She says that when it’s safe to do so and all of this crap is over, she wants to have yoga classes out there, maybe show movies and get the tiki bar going. Just have a gathering space where people don’t feel so lonely anymore, where people can reconnect. She’s got two bathrooms, one with a hand-painted mural of Dolly Parton, the other with a hand-painted mural of the late, great Divine. She cuts, her business partner colors, and they’ve always got good music playing. Last time, to my surprise, it was Hanson. You know what holds up? All of it, turns out.

People I know are making money however they can these days. They’re doing what they’ve always done, the things at which they are talented: bookkeeping, housecleaning, hairstyling, teaching, sex work, graphic design, freelance writing, masonry, hospital scheduling, nursing, firefighting, forestry, childcare, acting, pharmaceutical administration, all sorts of things. And they’re doing new things, things they’ve never done, things they don’t necessarily like, but they need the money. Sometimes it’s off the books. They get paid however they get paid.

I got to the end of my Venmo journey, skimming a lot of things because my time on earth is limited. But I had one Venmo-related question left. As my final act of research for this essay, I looked up a particular contact, to see if we’d ever exchanged money.

He was a TV and film editor. He was really good. He edited a lot of things you’ve seen, and some you haven’t. We dated a few years ago, but it didn’t work, so I didn’t talk to him for awhile because I was mad it didn’t work even though I had been the one to tell him it wasn’t working. I was mad because he agreed with me. I was mad because I knew I could love him, even though I didn’t, exactly, not then. But I wanted to, and I wanted him to love me in exactly the way I wanted him to love me, but he didn’t love me either, not yet. At least I don’t think so.

I am ashamed to say it, but I was using him to get over that aforementioned emotional affair. It didn’t work, of course. New lovers are not antibiotics to knock out the poison of sick love, and they are not vaccines against future infection.

But sometimes, if you’re very lucky, if it’s appropriate and healthy and all that good stuff you learn about in therapy, these exes become your real friends. And that is what happened, eventually. He reached out again, and we talked about going on more dates, but settled on being pals. What a lovely friendship it was, real and genuine and silly, devoid of tension or resentment.

He died two weeks ago, for no reason anyone can figure out yet, and it ripped me up. His best friend found him. I helped write his obituary, which was healing in many ways, and was a great honor for which I am thankful. But I can’t talk to him, and that’s hard. I miss him more than I can say.

Social media has certain records, though, of transactions of the financial sort and otherwise. While it is often a burden, I am grateful for it now. I got the phone call that he was gone, and I went looking for him again.

First, I went through old Instagram messages, all of them funny and tender, from Phase I (dating) and Phase II (friendship). I looked for Twitter direct messages, but there were none, because we unfollowed each other in a fit of pique at the conclusion of Phase I in 2017, when I was busy not showing up for my therapist or anyone else. It made me laugh and laugh, and I wish I could call him up and pretend to be mad about it. He would think it was pretty funny.

I looked at our emails, especially the Phase II ones, and there was one where he said he would always love me, and I said I would always love him. Nobody added AS A FRIEND, because we didn’t have to. Friends love each other, and if it was a little bit more than that for each of us, there was no need to highlight that part. I’m so glad for that exchange. He would hate that I told you about it, but I have to get used to the fact that he’s no longer here to love, or hate, or anything else.

Tonight, as I completed this essay, it occurred to me that he and I may have exchanged money over Venmo at some point — for the unromantic romantic trip we took to Big Bear, where we left Oktoberfest because it felt like (and was) a jubilant gathering of MAGA racists; for the countless times we hit up a taco truck or ordered pupusas or grabbed coffee; for anything, anything at all. He had been a whittler, and he made me a beautiful set of wooden sticks with which to hold up my hair, which he always loved. When we broke up, I snapped them in half and recycled them. I am unfathomably angry, irrationally so, that I did this.

But tonight I realized maybe we’d interacted on Venmo. Maybe we’d written a funny note or comment on said transaction. Maybe that would be left, the one digital keepsake I had yet to uncover.

Please, let us have engaged in the digital exchange of capital via a social networking application with horrible security practices. As if that would revive him, like a magic kiss. As if that would make me not miss him anymore.

I looked his profile up, and there he was, looking like himself in his icon. In the section where it shows one’s interactions with another user, there was — nothing. Nothing from me to him, and nothing from him to me. I guess we just used to treat each other. “You can get it next time,” I’d say, when he protested that I shouldn’t cover the cost of a meal. More often, he just paid for it himself.

I don’t sleep much at night anymore. I’ve had trouble with it since I moved back East in October, but it got much worse when my friend died, a couple days after the MAGA racists attacked the Capitol building.

People say that when Joe Biden took office, it was the first good night of sleep they’d had in months, or years. That was not my experience. I slept through most of the inauguration festivities. I had to text friends to ask, “Is he the president yet?” He had been the president for three hours already.

Grief is odd. I don’t think about my friend all the time, but the sadness isn’t in my brain. It’s in my bones. I get my work done, mostly, but I want to be asleep the rest of the time. I try melatonin, but it leaves me depressed the next day. I used to watch ASMR videos, but my two of my favorites turned out to be QAnon nuts (no surprise there). Sleeping pills seem like a slippery slope for a sober person, and I’d only try those if a doctor deemed it absolutely necessary for some reason. I’d rather avoid them.

Audiobooks used to help me drift off, but now I am acutely conscious that I don’t know how much time I have left, and I want to read all the books, absorb their stories, understand everything I can, before I’m gone. I stay awake listening to philosophy, to psychology, to ancient poetry.

And I watch you — not on Instagram, or on Twitter, or on Snapchat or TikTok or YouTube or Vimeo. I watch you on Venmo. I watch what you’re buying, and what you’re selling. I ponder your transactions, and your use of tiny pictures to describe them. What does that snowflake mean? What does that tree mean? What does that taco mean, really? I bet I know, I think, and chuckle mirthlessly, alone in my room.

Or I used to do that. Tonight I quit Venmo, right after I finished the first draft of this essay. It needed a new ending, so I gave it a better one. You can do that with essays, though not with people.

I quit because I don’t want to invent personalities for you anymore, or let the demons in my brain keep me up even later at night gossiping about why you sent that slice-of-cake emoji to that person on that date at that time. I don’t want to see how much you gave your ex-wife because your third kid, the surprise, needs braces. I don’t want to guess at what you’re doing for work. Whatever it is, I hope it’s going well.

If I know you, I want to really know you. If I love you, I want to really love you. And like I said, I have a limited amount of time.

Besides, I still have PayPal. And Zelle. And CashApp. And one day, if I’m feeling very wild and not so concerned about germs that could kill you, I may even start using real, physical dollars and coins again. None of those methods allows me to gain even a glimpse of what you’re up to in your not-so-private time. I can’t invent activities for you based on that scrap of info anymore. Maybe if I’m a good enough friend to you, you’ll tell me anyway.

I look forward to being the pain in the ass at the group dinner, the only weirdo without Venmo. In fact, I can’t fucking wait.

Curious

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Sara Benincasa

Written by

Author, REAL ARTISTS HAVE DAY JOBS (and other books). Writer of scripts. Host of WELL, THIS ISN’T NORMAL podcast. Patreon.com/SaraBenincasa

Curious

Curious

A community of people who are curious to find out what others have already figured out // Curious is a new personal growth publication by The Startup (https://medium.com/swlh).

Sara Benincasa

Written by

Author, REAL ARTISTS HAVE DAY JOBS (and other books). Writer of scripts. Host of WELL, THIS ISN’T NORMAL podcast. Patreon.com/SaraBenincasa

Curious

Curious

A community of people who are curious to find out what others have already figured out // Curious is a new personal growth publication by The Startup (https://medium.com/swlh).

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