Dating Expert Tells Us What To Do If You Get An Unexpected Venmo Request From Your Date

It's official: the dating world is a lawless land. Just like the Wild West where everyone was out for themselves by any means necessary, modern dating is no different. You may think you're on a date with someone kind and empathetic, then you wake up to a Venmo request from them and wonder what the heck just happened. Yes, this is a thing.

In news that shouldn't be totally shocking, this harmful dating trend has been picking up traction. It seems that men are paying the entire tab on dates, and then requesting half the bill after the fact. In the summer of 2023, CNBC reported on it happening to a woman in Brooklyn who was met with a Venmo request after denying a man a second date. But she wasn't the first to encounter such questionable conduct. In 2016, The New York Post talked to a handful of women who had also experienced the after-date Venmo request. It's certainly a bold move on a man's part considering the gender pay gap persists.

Although many of us can agree that this isn't just rude, but straight-up egregious behavior, that's not entirely the point. What really matters is how to handle it should it happen to you. In an exclusive chat with Women, professional matchmaker and co-CEO of Kelleher International, Amber Kelleher-Andrews gave us the 411 on exactly what to do if an unexpected Venmo request from a date comes your way.

While the dating world is rough, lawless terrain, invoicing for a date could come from two potential schools of thought. The first being that human decency is dead. "It's a byproduct of the awfulness and toxicity of online dating, where every first date is a blind date with a complete stranger," dating expert and author Jon Birger told CNBC. "There's zero social accountability, which makes it easier for people to behave badly." 

According to a 2020 survey by Pew Research Center, 67% of people report that their dating life isn't going very well and 75% believe dating is becoming harder and harder. The fact of the matter is that the result of this dating difficulty is clear: there are more single people than ever before, with the majority of people preferring singledom to being in a relationship.

Another reason could be economics. A 2022 survey by Lending Tree found that 19% of singles are going on fewer dates than usual because of inflation, and 77% feel that navigating the dating world would be easier if they had more money to shell out for dates. "Everything is getting more expensive," chief credit analyst Matt Schulz told Lending Tree. "Even a quiet night at home with a bottle of wine and some takeout is pricier than it used to be." While this may be a legitimate reason, it still doesn't necessarily make a Venmo request okay. 

Most tend to go into a date with an open mind and heart. As much as dating has become fairly insufferable, it's still a necessary step if we want to find a partner and fall in love. But just because you showed up, doesn't mean you have to stay if things get weird — especially if those things include being randomly charged for stuff you weren't expecting.

"If the date is that bad then the polity suggests it end after the next course," professional matchmaker and co-CEO of Kelleher International Amber Kelleher-Andrews exclusively told Women. "I am sure the feeling is mutual. It is not necessary to be rude and make someone feel ashamed or unworthy. It is even more ridiculous to charge someone in the present moment as if they are receiving a fine for not being your match." Should this happen to you, it's important to take your power back, according to Kelleher-Andrews, by stating your standards for them and yourself and asserting your boundaries. In other words, you're more than within your right to leave. "We do not exist for our dates to entertain us, we are on a date to connect, communicate, and relate," said Kelleher-Andrews.

If you manage to get through a date with no charges, lucky you! But in this day and age, a Venmo request may still be in your future. For example, if a man paid for the first date, but you declined a second, he might hit you up for your share of the first.

"Confronting a date about an unexpected Venmo charge can be challenging," Amber Kelleher-Andrews exclusively shared with Women. "If you wish to avoid drama in any conversation your rule of thumb is you stay calm and composed." While it may not be easy at the moment to remain level-headed, remind yourself that to take the high road and be the bigger person, it's essential. "Stay open to hearing their side of the story before jumping to any dramatic conclusions," said Kelleher-Andrews. When it's your turn to have the floor, express your surprise. "Make it clear that you are not comfortable with it and explain your own expectations regarding the date," Kelleher-Andrews told Women. "Ask in return for the reason behind the Venmo charge [...] It may be as simple as a misunderstanding [...] Depending on the outcome of the conversation, work together to find a resolution that feels fair."

If you decide the requester is being petty, you're under zero obligation to reimburse them. You're allowed to ignore it. Even if you didn't spend any money, your time and energy are worth something.

Although you may not be able to cure someone of all their bad behavior on a first date, you can do your best to get in front of situations — possible incoming Venmo requests included. "Remember, open communication is key in any relationship, including dating," professional matchmaker and co-CEO of Kelleher International, Amber Kelleher-Andrews exclusively told Women. "It's important to establish clear expectations and boundaries from the beginning."

While talking about money on a first date is considered taboo, and 44% of people feel that discussing it ruins chances for a second date according to The Balance, discussing how the bill will be paid is not. It's not unheard of to immediately decide if the bill will be split 50/50, exactly based on who ordered what, or if one person will be picking up all of it.

As Kelleher-Andrews pointed out, Venmo handles aren't public domain, but they're also not that difficult to find if your handle includes your first and last name. If your handle isn't something obvious, then she advised keeping such information to yourself. "Sharing your financial handle is your responsibility, and with this responsibility comes consequences and expectations," said Kelleher-Andrews. "Know your boundaries and don't give banking, financial, or personal handles to people you don't know and for reasons you can't predict." Unless, of course, it was agreed from the get-go that all the date's expenses would be split.