“What did we do before Venmo?” I recently said to my boyfriend, Jacob, as I clicked “request” on $17.56 for “groceries and quarters” I had picked up earlier that day. We dated for two whole years before we both installed Venmo, so I do know what our lives were like before we started relying on the convenient money app. Considering a lot of people have not carried cash for the better part of this millennium, the beginning of our relationship operated like most: on a see-saw of transactions. "I’ll get this one; you get the next." Every swipe of a credit card or breaking of a crisp new $20 from a rare trip to the ATM felt like a mini flirtation, as we signed receipts or pulled out loose bills to pay for late-night grilled cheeses and museum tickets. Venmo entered our lives during a very auspicious time: We had just moved in together. The complexities of sharing a home meant we had more important bills to split than a few dinners a week, and Venmo seemed liked the answer to prayers we didn’t know we had. Before we even had a chance to figure out how to divide and conquer our new joint living expenses the old-fashioned way, we devised a painfully millennial system around our new favorite app. Since I am OCD about paying bills, we decided our utilities would be in my name. I set up automatic monthly payments from my checking account and Venmoed (yes, it’s a verb now) Jacob for his half every month. Target runs became a breeze. “I’ll just get it and Venmo you later.” Either one of us could stop at the market for dinner fixings and Venmo the other for half of the receipt without a second thought. The equality we already felt in our emotional dynamic was now mirrored in the way we approached money. It became easy to split everything 50/50, so we did. As a result, the frequency with which we treated one another for no reason other than a gesture of love diminished into rarity.
The frequency with which we treated one another for no reason other than a gesture of love diminished into rarity.
Months rolled by, and it became increasingly automatic and expected to Venmo each other for every little thing, which worked out fine until every little thing added up to one really big thing. At the time, Jacob was freelancing, an inherently feast-or-famine pursuit. Luckily, I was leaning in big-time at work and picking up the slack during the famines was made easier with Venmo. Even though Jacob was unable to pay my requests while waiting on checks to roll in, I didn’t curb our spending habits. My stable income, plus the trusty bank of Venmo, was enough to keep me blindly spending for the both of us as if there was no fluctuation in cash flow. We didn’t need to change our lifestyle, because the app had become one virtual IOU. That’s all well and good if you live in the 1800s and the local general-store clerk keeps a written ledger of your credit and debit next to the register as long as you need him to. But it proved problematic in the 21st century when using a digital platform that deletes records after 90 days. News to us! Ninety days wasn’t always enough time for Jacob’s sometimes unpredictable clients to pay his invoices, and I wasn’t really paying attention because I knew he would take care of his half of each request when he could. I wasn’t worried because I had my favorite bank teller, Venmo, to keep track for me. But my heart froze the day I noticed the “incomplete” requests tab had been completely wiped. Hundreds of dollars waiting to be paid — gone. I frantically emailed support. Thankfully, they recovered a very precious PDF breakdown of my pending, incomplete requests. Unfortunately, reviewing the PDF took a lot of guessing since the transaction descriptions had been written in emoji, which translated into empty squares on the backlog — useless. New rule: no emoji. Another new rule (erm, rather an important relationship and personal-finance lesson): No spending income that hasn’t hit our checking accounts yet. The PDF of everything that Jacob owed me was sizeable — like, it spilled over onto a second sheet and needed an actual staple. Seeing it all laid out was a shock for both of us, especially when I added it all up and circled the total at the bottom of the sheet. Jacob felt overwhelmed, embarrassed, and disappointed in circumstances beyond his control that had led to this mess. But also, he was frustrated with me for spending money as if we were both still earning money. Fair. Very fair.
New rule: No spending income that hasn’t hit our checking accounts yet.
I had let things get out of hand and felt terrible about my selfish behavior. While Jacob was in a valley of freelancing, I was enjoying a peak of steady, well-paying work. I continued to spend money for the both of us — not thinking twice before buying $100 worth of succulents. Jacob was being very vocal about what he could and could not afford, but I was quick to dismiss him. “Don’t worry about it,” I’d wave away his financial concerns. I had been treating Venmo like Jacob’s loan officer: “Buy now, Venmo later. It’s all good, baby!” Maybe this is a good time to mention that I’m a fiercely independent only child, and sometimes I act like it — and not in a good way. I realized that if I were going to be in a true partnership, I couldn’t base all my decisions (and spending habits) on what worked just for me. More importantly, I needed to be more communicative and transparent about how I was spending our money, especially at a point in our careers that wasn’t totally in sync. I should never have put him in a position to feel embarrassed by two pieces of printer paper stapled together. Eventually, the checks came through. Jacob was able to repay every last cent, and we resumed using Venmo as we had before, albeit a little more cautiously, without letting requests expire into the 90-day abyss. But still, we’d been burned and stories of Venmo security breaches were starting to cause alarm — yet, not enough of a code red to stop using it altogether. Trying to figure out an equally seamless method of sharing finances as unmarried cohabitants seemed daunting. So, despite the glaring warning signs of scams and frauds, we kept moving forward dedicated to Venmo. Then, we hit the 2015 tax season. As Jacob began calculating his expenses, he realized that at least half of his write-offs — like our shared utilities, office supplies, and work-related meals — were tied up in Venmo transactions that had poofed away into the nothingness once they had been resolved. Luckily, I had kept track of the other half of most of them (via my very sound system of searching automatic bill notifications in my Gmail), but it was clear that it was truly time to rethink how Venmo fit into our relationship. Ultimately, we decided to keep using Venmo — only in a much more limited fashion. After all, it’s really meant to serve as a means to split the costs of fun activities with friends, not function as the main cog in a shared financial machine. Now, we use Venmo for small purchases, no longer relying on the app to carry the bulk of our money management. For that, we decided to open a new airline credit card with two authorized users. At the end of the month, we split the balance. This way we’re keeping better records, maintaining financial equality, and racking up travel points in the process. Also, throwing down one card to pay for the meal without an immediate Venmo request over dessert feels more spontaneous and romantic, even if we are just treating ourselves. Then again, in the time that I started writing this article, we got engaged and this whole new brilliant plan we devised — well, we may need to revisit it at some point soon. Maybe there’s a joint checking account in our future. And, no, there was no Venmoing involved in the purchase of my new ring, but Jacob did share that he wished he could have put the expense on our credit card to get the airline points. Fair. Very fair.