As Valentine’s Day celebrations begin, lovebirds everywhere are planning dates, exchanging gifts, and perhaps navigating the tricky waters of money in relationships. But how does money really impact matters of the heart, and how does the popularity of digital payments affect the proper etiquette of dating in the digital age?
We turned to Venmo’s passionate community of users across the country for their thoughts on how shared expectations can either help or hinder a successful date. To accompany the findings, revealing how Venmo is changing attitudes about once awkward financial discussions, we partnered with certified etiquette trainer and founder of Old Soul Etiquette, Mariah Grumet Humbert, to help navigate the proper payment protocol in today’s dating culture. Here’s a guide to Venmo etiquette when it comes to dating, straight from the Venmo community, so money doesn’t have to be a dealbreaker.
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Communication is Key: “Generally, the individual who initiates the date is responsible for covering the bill in its entirety unless the parties agree to split the bill ahead of time,” says Mariah Grumet Humbert, certified etiquette trainer and expert. “As the dating relationship develops, you can use Venmo more for splitting the bill or taking turns as long as that is discussed and agreed upon. Each relationship’s values and financial situation will look different.”
Be Mindful: “As the person on the date who did not initiate or make plans but accepted them, it’s not recommended to order the most expensive thing on the menu under the assumption that the person who initiated the date will be covering the bill.”
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Awkward Run-ins: “While there is no rule for how many dates you can or should go on in a certain time period, it’s best to space them out so you do not have any potential overlap, which could cause an awkward situation for you and your dates.”
Speak Up: “Sometimes the chemistry is off, but it’s best not to send a Venmo request for part of or the whole bill after a date unless splitting the bill has already been discussed beforehand so no one is caught off guard.”
Manage Expectations: “If you've initiated the date, it's important to have a conversation to understand your date's expectations for your outing so you can properly manage them. The initiator is responsible for choosing the venue for the date while considering their date’s preferences; this way they can choose somewhere or an activity they are able to pay for, such as a coffee date instead of a formal restaurant.”
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Tipping Appropriately: “A good rule of thumb is to tip 18-20% when dining out or when you have run up a larger bill for cocktails.”
Venmo’s Bad Date Rebate
Most of us have experienced a bad date or two in the game of love. This Valentine’s Day, Venmo is helping people bounce back and give the dating game another shot with some extra money in their pockets.
We’ve teamed up with the ‘Rebate Squad,’ including Love is Blind star Monica Davis whose ‘cha-ching’ on Venmo was heard round the world, and social media stars, Eric Sedeño and Stef Dag, to hear your bad date stories. From now through Feb. 14, you can drop your story in the comments of Venmo’s Instagram Reel for a chance to receive $250 in your Venmo account which can be put towards a date to find love again.
Research Methodology: Venmo commissioned Atomik Research, an independent creative market research agency, to run an online survey of 1,004 adults in the United States who are Venmo users. The margin of error fell within +/- 3 percentage points with a confidence interval of 95%. The fieldwork took place between January 31 and February 3, 2025.