A Guy Requested $20 From Her On Venmo Several Hours After Their Date Ended

In recent years, a new dating trend has arisen regarding money requests. Apparently, more men are getting into the habit of asking women to reimburse them if a first date doesn’t go anywhere.
TikToker Kate (@8kateee) is spilling the details about the worst dating experience she’s ever had, where a guy requested $20 from her on Venmo several hours after their date ended.
In 2020, she lived in Milwaukee, Wisconsin, a city she was not a huge fan of. So, when a guy from Chicago messaged her, she saw it as the perfect opportunity to leave Milwaukee just for a day. The plan was for her to drive to Chicago in the morning, hang out with him, and return home in the afternoon.
For their date, he decided that they would ride bikes on the lakefront. During their bike ride, he fell off his bike twice.
She was confused as to why he had planned a date that centered around bikes when he clearly didn’t know how to ride one.
They also hung out at his pool, and later, they got dinner and drinks. They were having a great time, but after dinner, it was starting to get pretty late.
So, she told him she needed to grab her stuff from his apartment and asked if he could walk her back to the parking garage where she had parked her car.
He begged her to stay and watch one episode of a TV show with him. She declined and reminded him that she had to drive all the way back to Wisconsin. Still, he wouldn’t let up, which made her uncomfortable.
When she got home, she told him over text that his insistence on her staying at his apartment on a first date made her uncomfortable.

Julia – stock.adobe.com – illustrative purposes only, not the actual person
That’s when she received a Venmo request for $20. A screenshot of their conversation showed that she texted back, “Are you serious?” He responded with, “What?”
She pointed out that $20 wasn’t even enough to cover a quarter of the costs for the bike rentals, dinner, and drinks.
So, to her, the Venmo request seemed like he was retaliating against her for being called out on his actions. She ended up making the payment because she didn’t want to speak to him ever again.
She also revealed in the video’s caption that he “slid into her friend’s DMs” even though he knew they were friends. Many TikTok users shared the ridiculous requests that men they’ve gone out on dates with have made.
“Once a man Venmo requested me for half of a soft pretzel, and I went on to date him,” admitted one user.
“In college, a guy buys me two drinks and harped on me for paying him back $12. For TWO MONTHS,” commented another.
“Back in 2019, a guy invited me out for drinks, and he asked if I wanted wings…he sent me a $3 cash app request,” wrote a third.
@8kateee Then he slid into my friends DMs, knowing we’re friends?#firstdate #baddatestory #chicagodating
Sign up for Chip Chick’s newsletter and get stories like this delivered to your inbox.
More About:Romance