It happened more than once. I would be invited to a relatively lavish restaurant - a romantic bistro with soft lighting, wines sourced from postcard-perfect vineyards - a place that I would not 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 message from my date asking for my Venmo username so we could split the bill.
With financial technology like Venmo, an app for easily sending money back and forth, it is simple to send a quick request to cover any costs, from a cup of coffee to paying rent. It is so easy that it has become hard to tell when your partner or date is treating you to a night out or when you are expected to cover half the cost.
There were more than 40 million active Venmo accounts as of this year's first fiscal quarter, according to PayPal, which owns Venmo.
That is 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 have had hurt feelings and confusion over money requests for nights out that had felt like a gift or a treat at the time. The problem was not that my partner wanted me to pay him back - it was that I had not 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 is the person who should pay," said Ms 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."
"But every couple's different. Every date is different," added Ms Meier, noting that gender is becoming 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", she 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.
What is too small an amount to even bother asking for someone to contribute?
Ms Sable Tannahill, 28, regularly exchanges money with her partner in Portland, Oregon, via Venmo. "I'm not expecting to be paid back for every little thing, but I think some people use Venmo that way," she says, referencing an acquaintance who can seem passive-aggressive when requesting what she calls tiny amounts of money on the financial platform.
If anything, her partner sends her money via Venmo when she is not expected or asked to, even when the baseline amount is about US$10 (S$14), which is what Ms Tannahill says she considers to be the lowest amount worth reimbursing.
Over the holiday scramble, though, Ms Tannahill felt the pair was requesting the same US$50 from each other repeatedly, as celebrations, gifts and plane tickets piled up and reimbursement became a Groundhog Day-esque loop. "Does anyone owe anyone any money at that point?" she says.
If multiple large expenditures are coming up, you can estimate how much each item will cost, then divide 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 are asked to pay for half of the holiday flights or half of a bottle of wine from the grocery store, it is important to fulfil requests in a timely manner. "Right then and there is the right time to pay someone back if you have the ability to," says Ms Meier. "If someone (pays) a restaurant bill, right then and there you can take out your mobile phone and pay him back."
Exceptions apply, of course, if you have had a conversation with the other person and set a longer payback period.
Ms Meier believes a 24-hour reimbursement through the app is most courteous. If someone has not paid you back after a few days, it is okay to check in about it or use the app's reminder feature, she says.
Sending and receiving money via the app does not 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 cannot appear in person to do the cheering.
My experience with Venmo has not been only negative: My boyfriend, who is not local, has made similar generous gestures, sending me money for sick-day snacks or dinner delivery when I am having a stressful day.
It is his way of showing he cares when he cannot be nearby.
• The writer is an editor at publisher SmartBrief.