Man paid the full $140 bill on their third date after she offered to split — then her $5.50 Venmo request the next morning made him question a fourth
Each person has different views about finances when it comes to dating. These should be discussed in advance to avoid disappointment. A man who goes by u/TARDIS_909 shared a Reddit post on Monday, October 26, 2026, revealing how a seemingly nice third date ended up likely being his last one with a woman. They had a great time at dinner, and being a gentleman, he paid the entire $140 bill without any expectation. The next day, he was surprised to find a $5.50 Venmo request from the woman.
paid for an expensive 3rd date dinner and just woke up to a $6 Venmo request from her?
by u/TARDIS_909 in dating_advice
The duo went to a nice Italian restaurant that the woman had picked. The bill amounted to $140, and even though she offered to split it, the man assured her he had no problem paying the entire thing. They continued walking after dinner, and the woman decided to stop at a convenience store and pick up sparkling water and gum. Before he could get his card out, she tapped and paid $11 in total. The date ended on a good note, and they both returned home. The next day, the man woke up to a $5.50 Venmo request with a sparkling water emoji, half of the $11 she had paid at the store. The man was unsure how to comprehend the situation. It wasn’t that he had to pay, but rather that she wanted to split such a meager amount.
“Does this mean she views me purely as an acquaintance? Or is this just some weird modern etiquette where people track every single cent down to the wire?” he remarked. The event made their interaction awkward, and he had no idea how to respond or take things further. People in the comments suggested he also ask her to pay her share of the dinner bill. u/Manners2210 wrote, “It’s not the cost, it’s just a weird mindset that paints an ominous sign of things to come.” u/datingnoob-plshelp added, “I would send her a screenshot of the request to her and say, ‘Hey, I want to double-check if this is you?’” u/VegetableProblem222 remarked, “Reply with a Venmo request for $64.50.”
Whatever the idea of a date, expectations should be communicated, especially when it comes to splitting the bill. Vague explanations can lead to misunderstandings and disappointments later. In another instance, a woman went out on a date with a man and was shocked when he asked if they could split a $60 bill. She was taken aback but didn’t mind paying $30. However, when she agreed, he started listing the things he had ordered and decided to pay only for those, leaving her even more confused.
She noted that she had not ordered something extraordinary that would justify splitting the bill that way. Furthermore, since nothing was discussed beforehand, she was under the impression that he would be paying since he had asked her out and picked a place. The difference in their bills was only $1, but the man ensured he pointed that out to the waiter. It changed her entire perception of their date and their potential relationship.
You can follow u/TARDIS_909 on Reddit for more stories.