I don't know about your friend group, but in mine, the shameless $2 Venmo request, which I have both sent and received countless times, has usurped the "what's mine as yours" mentality of old. In 2018, there were over 3 million transactions of under $1 on Venmo. A chunk of those were probably sent in jest, but that's still a lot of petty. And when you add in the social feed element, which makes it really easy to keep tabs on your ex's financial behavior — welp, it's kind of a breeding ground for drama.
That's why we asked 12 women to share their juiciest (and cringiest) Venmo stories. Read on for timeless tales of what not to do on everyone's favorite financial app.
Location: New York City
"A year ago, I started seeing a married man without knowing the extent of his relationship and family dynamic. I immediately broke it off when I found out that he actually wasn’t separated from his wife, and I deleted his number. Because he knew his wife knew my number, he started messaging me via Venmo comments! He would literally pay me a small transaction and make it private, then type out his feelings in the comment of the transaction trying to get me back.
My friends were all amazed that Venmo was becoming the new 'cheating' platform. This continued for a few weeks with dozens of comments before I eventually made my Venmo private. Needless to say, we don’t talk anymore, but my friends still talk about him ruining his marriage through Venmo."
Location: New York City
"I got tickets to Hamilton for a decent price in a pre-sale and invited my ex-boyfriend to visit for a weekend and see it. We’d always talked about it and I needed sex, so it happened. He paid me for his ticket on Venmo and left it public, so all our friends — Oh! And my BOSS — called me out on it. After the weekend, I had to answer more questions about why I’d gone with him than about what I thought of the musical. "
Location: Syracuse, NY
"In my 20-person friend group, for everyone's birthday we get a group gift — something within the $10-$12 (per person) range. While it does add up to roughly $200 a year, all the gifts are super thoughtful and everyone gets one, so it works out in the end. There is one girl who NEVER Venmos her portion of the gift, even though she received an amazing one for her birthday. While it's just $10, it really adds up over time. She never declines joining in on the gift, but ignores the initial Venmo request and the reminder. I have handled the last two gifts (which she has not contributed to), and I have been encouraged by other girls in the group to confront her, but I genuinely don't care enough to make it awkward between us."
Location: Washington, D.C.
"During my senior year of college, I was living with two friends — one of whom my other friend and I had been on increasingly worse terms with for the entire summer and into the first semester. The final straw was when I Venmo requested her $4 for toilet paper and paper towels and she declined it. I started locking the toilet paper in my room after that."
Location: Brooklyn, NY
"I've discovered an ex of mine was dating someone new via Venmo and I've been discovered as dating a new person by an ex who was Venmo-stalking me. The ex who made the discovery that I was dating someone new wasn't on Facebook, Instagram, Twitter, or any social media, and we didn't really have any mutual friends, so I assumed he was unaware of my new relationship status.
We were texting, and I had to be like: 'FYI I have a boyfriend now.' He very coldly replied: 'I know, I have Venmo.' Perhaps counterintuitively, that made me commit to leaving my Venmo transactions public — transparency can be very helpful!"
Location: Texas
"My last semester in college I was out of options for housing, so I ended up moving in with some roommates from Craigslist. They were super frugal (they never told me this before I moved in) but also wouldn't let me chip in for bills. It was super weird. Anyway, after moving out, I was stalking one of their accounts and found multiple transactions between them calling me a demon and criticizing me for hiking the utility bills up. They could have just asked me — I totally would have pitched in! Yikes."
Location: New York, New York
"I was over at a friend’s house a few years ago. We were relaxing and having a few beers that my friend had stocked in the fridge. I literally had ONE bottle. She never mentioned that we had to pay her for the beer. The next morning I woke up to a $5 (!!!) Venmo request from her for the beer. Excuse me? She’s always been cheap, even though she has money. I paid it and never spoke to her again."
Location: Washington, D.C.
"When I was a sophomore in college, my ex-boyfriend and his friend got drunk and started Venmo paying one another. My ex paid his friend saying 'We hate D.' (his friend's ex), followed by his friend paying him saying, 'We hate Layla.' I commented on it saying: 'You guys know this is public, right?'
To make it WORSE, his friend messaged me on Facebook after and was like: 'I swear this was about my dead dog, which is why it was spelled Layla not Leyla! I know that sounds crazy but it was! Here's a picture!' And she did include a picture. This was so odd to me — why would you Venmo someone saying you hated your deceased dog? I ended up texting my ex to tell him that it was really cruel and unfair, and he told me that I was overreacting. Years later we are friends again, but I will never forget how strange this experience was (and I'm pretty sure he never unblocked me on Venmo after this incident)."
Location: New York, New York
"While I was on vacation, the girl I was dating went to a lesbian party and cheated on me with someone but told me that nothing happened. She then asked me to be in an open relationship so she could text that girl. I said I'd think about it, and then while I was thinking about it, she broke up with me anyways (v rude, broke my heart, whatevs). Literally ONE DAY after she broke my damn heart, I saw on Venmo that she was getting drinks with the girl she cheated on me with, who I obviously then stalked a lot. I ended up blocking my ex on Venmo and we haven't spoken in years."
Location: Chicago, IL
"I saw that my ex, with whom I was once in a long-distance relationship, sent his roommate a 'last rent' payment. I initiated the break up, but we had seen each other a couple times in the year and change since, and have been cordial. Curious, I sent him a friendly text admitting to Venmo reconnaissance and asking where to. He responds: 'Yeah, I'm actually moving back [to where I lived at the time]. I thought about telling you, but I didn't want to give the wrong impression.'
UGH! Excuuuse me, but I'm not over here pining. I wouldn't have even expected him to tell me in the first place. Overthinking it or not, it felt like a slap in the face. Somehow I held all these thoughts back and replied with a passive-aggressive: 'Okay!' We ended up running into each other a couple times and have had friendly encounters, but I haven't seen a Venmo transaction since."
Location: Philadelphia, PA
"I went on a first date with a guy to a haunted house. He bought the tickets, so I was planning to offer to pay for drinks before. As I took out my credit card, he told me I needed to pay since he bought the tickets. Later, we Ubered back to our part of town (we lived a few blocks from each other) and he made me call the Uber. A week later, he sent me a Venmo request for my half of the tickets! I ended up accepting and then charging him the same amount for drinks and the Uber. We did not go out again."
Location: San Francisco, CA
"A friend of mine had recently moved across town, and we arranged for me to come see her new place. As a housewarming gesture, I brought her two bottles of wine and proceeded to pay for transportation to her new place (a roundtrip cost of at least $30). On my way to her apartment, she suggested that we order a pizza for dinner — I obliged and she let me know that she'd put in an order for delivery. When I arrived, we cracked open one of the wine bottles I brought and proceeded to catch up on life. When the pizza was eventually delivered, she put together a small salad for us to start with, and we eventually moved on to the pizza. It was a normal, no-drama evening. Enter Venmo.
"A day or two later, she charged me $30 for what I assumed to be half the cost of the pizza. A MEDIUM pizza. In what universe (even including tip) is a medium pizza $60?!?! I knew if I were to confront her about it I'd come off as super passive-aggressive, so I swallowed my frustration and wrote it off as a fluke. In the time that's passed, I've come to understand that she's an incredibly cheap person who'd jump off a cliff before offering to pay for someone else. I have no idea how much that pizza actually cost, but I wish I'd asked."
Like what you see? How about some more R29 goodness, right here?
The Official Guide To Venmo Requesting Etiquette