My Date Insisted on Paying the Bill — I Wish I Hadn’t Let Him

My Date Insisted on Paying the Bill — I Wish I Hadn’t Let Him

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.

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.

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.”

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.”

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.”

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.”

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.”

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!

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