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I wish I hadn’t allowed my date to insist on paying the bill.

By World WideApril 20, 2025No Comments5 Mins Read
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My acquaintance arranged for me to go on a date with this guy.

He arrived with flowers. Real roses, not a bunch from the grocery store.

The dinner was excellent. He helped out my chair, unlocked doors, and was nice. I made the grave error of reaching for my wallet when the check arrived.

He put his card down and responded, “Definitely not.” “On the first date, a man pays.”

I thought it was one of the greatest first dates ever when I left.

Until I noticed that he had sent me a bill the following morning.

It’s not just a message. A real, detailed bill for my portion of the meal. with tip and tax included.

I initially believed it to be a joke. Perhaps a strange, arid sense of humor. However, when clicking the URL he sent, I saw that it was a legitimate Venmo request for precisely $68.42.

I looked incredulously at my phone. Was this man being serious?

“Hey, is this a joke?” I messaged him.

Without hesitation, he said, “No joke. Women shouldn’t be allowed to feel they can simply grab free lunches, in my opinion. I made the payment out of courtesy, but now that the date is over, I demand justice.

I felt sick to my stomach as I blinked at the screen. Forget about chivalry.

I could afford the money, so I wasn’t really upset about it. It was the idea. He had shut me down when I offered, and he had made such a show of paying. And now? He demanded his money returned now, as if I were a fraudster?

“You made it very clear that YOU were paying,” I said after taking a long breath. I made an offer.

His response? Yes, I did want to know if you were the type of lady who simply expects to be taken advantage of. I know now.

Oh. He wants to put me to the test?

Even though I could feel my blood pressure increasing, I inhaled deeply again. It’s not worth it. I disregarded the payment request, blocked his number, and carried on with my day.

It ought to have ended there. However, it wasn’t.

My friend, who arranged our meeting, emailed me a few hours later to ask, “What happened with you and Kevin? He just made a tirade about you on the internet.

I let out a grunt and clicked on the link she provided.

The Facebook post was made public. A lengthy tirade about “feminists who claim they want equality but still expect traditional dating norms when it benefits them” and “modern women who use men for free meals.”

What’s the worst? I was tagged by him.

I almost dropped my phone. In fact, he dared to attempt to publicly humiliate me.

A mix of individuals were laughing at him and encouraging him in the comments, most of whom were his buddies. Some even saw my profile and began sending me messages like “Hope that steak was worth it, gold digger” and “Pay the man back, princess.”

I was fuming.

I initially considered ignoring it. But then I thought—fuck that. Did he want an answer? He intended to obtain one.

I snapped a screen grab of his post, his Venmo request, and our texts. I then penned my own:

“Watch out for Kevin [Last Name], ladies. He demanded payment for our date, and the next morning, he emailed me a Venmo request for my portion. He shamed me in public when I refused. Avoid dealing with someone who engages in social experiments rather than building real relationships.

My post became viral in a matter of minutes.

Women began posting their own terrifying tales about men like Kevin in their comments. Some even mentioned their personal experiences after recognizing him. As it happens, he had already done this to other women.

Then something unexpected occurred.

Kevin sent me another message.

Whoa. Are you going to damage my reputation in public? All due to your inability to pay your fair share?

“Oh, you ruined your own reputation, buddy,” I texted back, laughing. I just gave the receipts to you.

I didn’t hear from him again after that. By the time he removed his post, the harm had already been done. His name was already being circulated as a walking red flag in local Facebook groups.

My friend apologized profusely for ever introducing us a few days later. She was unaware of his personality.

Lesson learned: It could be a setup if someone is extremely kind on a first date. And if you have a strange feeling about someone, always, always follow your instincts.

And Kevin, too? I hope that $68.42 was worthwhile if you’re reading this.

Have you ever had a date go horribly wrong? Post your tales in the comments section! Additionally, if you liked this post, please remember to like it!

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