I went on a date with a guy my friend set me up with.
He showed up with flowers. Not a cheap grocery store bunch—actual roses.
Dinner was perfect. He was charming, opened doors, 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 sent me a bill.
Not just a message about it. An actual itemized invoice for my share of the dinner. With tax and tip calculated in.
At first, I thought it was a joke. Maybe some kind of weird, dry humor. But when I clicked on the link he sent, it was a real Venmo request for exactly $68.42.
I stared at my phone in disbelief. Was this guy serious?
I sent him a message: “Hey, is this a joke?”
His response came instantly: “No joke. I don’t believe in letting women think they can just get free meals. I paid as a courtesy, but now that the date is over, I expect fairness.”
I blinked at the screen, my stomach twisting. So much for chivalry.
I wasn’t even mad about the money itself—I could afford it. It was the principle. He had made such a show of paying, even shutting me down when I offered. And now? Now, he wanted his money back like I was some kind of scammer?
I took a deep breath and replied: “You made it very clear that YOU were paying. I offered.”
His answer? “Yeah, well, I wanted to see if you were the kind of woman who just expects a free ride. Now I know.”
Oh. Oh, he wanted to test me?
I could feel my blood pressure rising, but I took another deep breath. Not worth it. I blocked his number, ignored the payment request, and went about my day.
That should have been the end of it. But it wasn’t.
A few hours later, my friend—the one who set us up—texted me: “Uh, what happened with you and Kevin? He just posted a rant about you online.”
I groaned and clicked the link she sent.
It was a public post on Facebook. A long-winded diatribe about “modern women who use men for free meals” and “feminists who claim they want equality but still expect traditional dating norms when it benefits them.”
And the worst part? He tagged me.
I nearly dropped my phone. He actually had the audacity to try and shame me publicly.
The comments were a mix of people laughing at him and others—mostly his friends—egging him on. Some of them even found my profile and started messaging me things like, “Pay the man back, princess,” and “Hope that steak was worth it, gold digger.”
I was FUMING.
At first, I thought about ignoring it. But then I realized—screw that. He wanted a response? He was going to get one.
I took a screenshot of our texts, his Venmo request, and his post. Then I wrote my own:
“Ladies, beware of Kevin [Last Name]. He insisted on paying for our date, then sent me a Venmo request the next morning for my share. When I refused, he publicly shamed me. If you don’t want to deal with someone who conducts social experiments instead of having genuine connections, steer clear.”
Within minutes, my post took off.
Women started commenting their own horror stories of guys like Kevin. A few even recognized him and added their own encounters. Turns out, I wasn’t the first woman he’d done this to.
Then, the unexpected happened.
Kevin messaged me again.
“Wow. So you’re going to publicly ruin my reputation? All because you couldn’t handle paying your fair share?”
I laughed and typed back: “Oh, you ruined your own reputation, buddy. I just shared the receipts.”
That was the last I heard from him. He deleted his post, but by then, the damage was done. His name was already circulating in local Facebook groups as a walking red flag.
A few days later, my friend apologized profusely for ever introducing us. She had no idea he was like that.
Lesson learned: If someone is over-the-top nice on a first date, it might just be a setup. And always, always trust your gut when someone gives you a weird vibe.
Oh, and Kevin? If you’re reading this—I hope that $68.42 was worth it.
Ever had a date go unexpectedly bad? Share your stories in the comments! And don’t forget to like if you enjoyed this post!