It happened more than once. I’d be invited out to a relatively lavish restaurant — a romantic bistro with soft lighting, wines sourced from postcard-perfect vineyards — a place that I wouldn’t suggest as the scene of one of even the first 20 dates with a prospective partner.

Each time I was invited to such a place for a first or second date, I would feel rather flattered at the extravagance. Until the next day, when I would receive a text from my date asking for my Venmo username so that we could split the bill.

With financial tech like Venmo, an app for easily sending money back and forth, it’s simple to send a quick request to cover any costs, from a cup of coffee to paying rent. It’s so easy that it’s become hard to tell when your partner or date is treating you to a night out or when you’re expected to cover half.

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There were more than 40 million active Venmo accounts as of this year’s first fiscal quarter, according to PayPal, which owns Venmo. That’s a lot of shared pizzas and bar tabs. While Venmo can make splitting bills easier, it also has the potential to provoke pettiness. So how can you use Venmo without killing the romance or feeling like a penny pincher?

In my current relationship, I’ve had hurt feelings and some confusion over money requests for nights out that had felt like a gift or a treat at the time. The problem wasn’t that my partner wanted me to pay him back — it was that I hadn’t known it was something he wanted me to contribute to, like the time he sent me a Venmo request for something as small as a cup of hot mulled wine at a Christmas market that he had suggested we attend.

“Whoever invites out is the person that should pay,” said Myka Meier, founder of Beaumont Etiquette, an etiquette school with offices in New York and California, whose clients are primarily millennials and Gen Xers. “If you pick the restaurant, pick the wine, pick the whatever, then you’re the one who might want to consider picking up the bill.”

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“But every couple’s different, every date is different,” added Meier, noting that gender is becoming less and less of an indication of who will pay the bill. “Something I think that people get surprised about — and I would agree with this — is when you get that request after the date that you weren’t expecting.”

Then what do you do?

Erin Lowry, an author and personal finance expert who runs Broke Millennial, says a lack of financial communication can go beyond Venmo requests — and can be a sticking point in platonic relationships, too. Money is “still quite a secret and taboo topic,” Lowry says, stressing the importance of communication. Talk about what you might be splitting before or at the time of purchase instead of charging someone later, she advises. Otherwise “there’s a certain passive-aggressiveness to just sending a request for money without having a conversation,” she adds. Without a conversation upfront, even romantic partners seem like faceless debt collectors.

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What’s too small an amount to even bother asking for someone to contribute? Sable Tannahill, 28, regularly exchanges money with her partner in Portland, Ore., via Venmo. “I’m not expecting to be paid back for every little thing, but I think some people use Venmo that way,” says Tannahill, referencing an acquaintance who can seem passive-aggressive when requesting what she calls tiny amounts of money on the financial platform.

If anything, Tannahill’s partner sends her money via Venmo when she isn’t expected or asked to, even when the baseline amount is around $10, which is what Tannahill says she considers to be the lowest amount worth reimbursing.

Over the holiday scramble, though, Tannahill felt that the pair was requesting the same $50 from one another repeatedly, as celebrations, gifts and plane tickets piled up and reimbursal became a Groundhog Day-esque loop.

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“Does anyone actually owe anyone any money at that point?” she said with a laugh.

If multiple large expenditures are coming up, you can estimate how much each item will cost and then divvy up the tasks instead of splitting each one down the middle. That also saves time later spent figuring out who owes whom how much.

Regardless of whether you’re asked to pay for half of the holiday flights or half of a bottle of wine from the grocery store, it’s important to fulfill requests in a timely manner. “Right then and there is the right time to pay someone back if you have the ability to,” said Meier. “If someone [pays] a restaurant bill, right then and there you can take out your phone and pay them back.”

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Exceptions apply, of course, if you’ve had a conversation with the other person and set a longer payback period. Meier believes a 24-hour reimbursal through the app is most courteous. If someone hasn’t paid you back after a few days, it’s okay to check in about it or use the app’s reminder feature, she says.

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Sending and receiving money via the app doesn’t necessarily have to be an anxiety-inducing concept. Some have taken to social media to showcase their partner generously sending them money for drinks, coffee or a trip to the nail salon. A small, spontaneous gesture can easily brighten your partner’s day, especially if you can’t appear in person to do the cheering.

My experience with Venmo hasn’t only been negative: My boyfriend, who isn’t local, has made similar generous gestures, sending me money for sick-day snacks or dinner delivery when I’m having a stressful day. It’s his way of showing he cares when he can’t be nearby.

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