After a great first date, she got a 2:45 a.m. Venmo request for $24.11 in drinks — then his reason left her in disbelief
A first date can end with a simple goodbye, further plans, or even a notification that changes the story of the evening. One woman named Angi recently found herself dealing with the last option after checking her phone in the early hours of the morning. Angi later shared the experience on Instagram, where she explained what happened after meeting a man for drinks. The video, shared on May 19, 2026, featured her sitting casually in her car while she revealed screenshots of the conversation to viewers. Posted under the handle @angi.jamz, the clip showed a late-night exchange that left her visibly shocked.
The messages arrived around 2:45 a.m., long after the date had ended, and the conversation took a surprising turn almost immediately. The exchange began when the man sent a message asking, “Hey, could you Venmo me $24.11 for the drinks I paid for?” Angi appeared surprised by the request, especially since there had been no disagreement during the date itself. In the middle of the conversation, the man admitted he would not have paid for the drinks if he had known she was not going to sleep with him, revealing his true intentions. He reportedly later suggested she would not need to send the money if she changed her mind and decided to visit his place instead.
He also repeated that he felt entitled to reimbursement because the evening had not gone the way he expected. The messages left little doubt about why he was asking for the money. As more screenshots appeared on screen, Angi covered her mouth in disbelief while reading the messages. The man continued to explain his position and pointed to bikini photos on her profile as part of the reason he had formed certain expectations before the date. He later wrote, “Kind of unfair to lead me on,” while insisting that she repay him. Respect for another person's choices should never depend on assumptions made beforehand. In the caption accompanying the video, Angi also revealed that she had not sent him any money.
The chemistry on a first date can be real, but so can the disappointment that follows. This is what another woman named Kylie Hill experienced in a recent incident. After matching online, Hill spent about two weeks talking with a man through messages and video calls before they finally met in person. The date went well, and she felt they had a genuine connection. Looking back on the evening, she said, “He is lovely, we get on very well.” The pair enjoyed dinner together and continued spending time together afterward. She even recalled that they “had so much fun” during the night.
When the date ended, she felt positive about where things might go next and hoped to hear from him again soon. Later, she received a message from him and initially felt excited to see his name appear on her phone. However, her excitement quickly disappeared when he asked if she was “comfortable sending feet pics.” The unexpected request made her reconsider the impression she had formed of him during the previous weeks. “This is why I don’t date,” she later added.
For more interesting dating stories, follow @angi.jamz on Instagram.