I went on a date with a guy my

Dinner was perfect. He was charming, opened doors, and pulled out my chair. When the check came, I reached for my wallet—big mistake. “Absolutely not,” he said, sliding his card down. “A man pays on the first date.” I walked away thinking it was one of the best first dates ever, until the next morning, when I saw that he’d sent me a Venmo request for half the bill.

At first, I thought it was a joke. Maybe some kind of flirty way to keep the conversation going. But there was no playful emoji, no winking message. Just a cold request for $42.50.

 

I stared at my phone, debating what to do. Should I pay it? Should I call him out? Should I just ignore it and move on? My friend, the one who set us up, laughed so hard when I told her that she nearly choked on her coffee. “No way!” she wheezed. “The same guy who gave you the ‘A man pays on the first date’ speech? What a legend.”

I decided to respond. “Hey! I got your Venmo request. Just curious, was that a mistake?”

He replied within minutes. “Not a mistake. I think it’s fair to split things.”

I was stunned. “But you literally said ‘A man pays on the first date.’”

“Yeah,” he wrote. “But I meant, like, at the moment. You offered, and I turned it down because it would have been awkward in front of the waiter. But I figured after the fact, splitting was fair.”

I had to laugh. I mean, the mental gymnastics! I screenshotted the conversation and sent it to my friend. “I cannot with this guy.”

She replied: “You have to tell him. You have to call him out.”

I thought about it, then decided I would. I messaged back: “Honestly, I would’ve been fine splitting if you’d just said so from the start. But don’t act like some old-school gentleman and then send a charge request the next day. That’s weird.”

He left me on read.

I figured that was the end of it. I mean, lesson learned. But then, a week later, my friend texted me: “Omg. Check your Venmo.”

I opened the app and saw that he’d not only deleted the request but sent me $42.50 with a message: “You’re right. That was weird. My bad.”

And just like that, I felt a little better about humanity.

I didn’t reply, but I did smile. Not because I’d gotten my money back, but because people—even the ones who make dumb mistakes—are sometimes capable of growth.

And that’s the lesson, I guess: If someone does something that feels off, don’t be afraid to call them out. You might not always get an apology, but sometimes, you do.

And sometimes, you even get $42.50 back.

If this story made you laugh, roll your eyes, or just shake your head at modern dating, share it with a friend! Who knows, maybe they’ve had a Venmo-date disaster of their own.

Related Posts

Devastated After Burying My Wife,

At 34, I was a grieving widower raising our 5-year-old son, Luke. My wife Stacey had died in a car accident—at least, that’s what her parents told…

My Dad Kicked Me Out for Marrying a Poor Man

“If you marry him, you’re no longer my daughter.” Those were the last words my father said before walking out of my life. I chose love over approval—Lucas,…

A barefoot little boy was concealed in the bathroom of our plane

On what was supposed to be a routine flight, everything changed when I opened the airplane bathroom door and found a barefoot little boy inside. His clothes…

Teacher gets kicked out for

Julia presented herself in a simple and unembellished outfit, marking a significant change while filming emotional scenes for August: Osage County in Bartsville, Oklahoma. On set: Actress…

Blinded by the Light? 90% of Drivers Say LED

Modern vehicles often feature LED headlights, which are praised for their energy efficiency and modern appearance. However, these lights have caused rising anxiety among drivers, with almost…

Suspect in Frisco Track Meet Stabbing

A tragic incident occurred at a high school track meet in Frisco, Texas, on April 3, when 17-year-old Austin Metcalf was fatally stabbed by Karmelo Anthony, also…