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

When Eric insisted on paying for our first date, I genuinely thought I’d met a rare gentleman. He showed up with a bouquet of roses, a small wrapped gift, and a charming smile. Mia, my friend who set us up, had raved about him. She was certain we’d click. And to my surprise, we actually did.

Dinner was delightful. Eric was engaging and attentive, asked questions, and even remembered details from our previous texts—like my favorite dessert and how I took my coffee. He opened doors, pulled out my chair, and complimented my outfit in a way that didn’t feel forced. When the bill came, I instinctively reached for my wallet, but he quickly waved me off and confidently said, “A man always pays on the first date.” I thanked him, flattered, and left feeling it might have been one of the best first dates I’d ever had.

Then came the next morning.

At 8:07 AM, I received a text from Eric. Expecting a sweet follow-up or maybe a request for a second date, I was instead greeted by… an invoice.

Yes, an actual itemized invoice. Listed were “charges” for the roses ($12.99), the small gift ($9.50), pulling out my chair ($1.00), opening the car door ($1.50), and the dinner itself. But here’s where it got bizarre—each item had a required “repayment” method. A hug for the flowers. A selfie for the gift. A “long conversation about feelings” for pulling out my chair. And for dinner? A guaranteed second date.

At the bottom of the invoice, in bold, it read:
Failure to comply may result in collections. Chris will hear about this.

I was stunned. Was this a joke? Sarcasm? I stared at the message for a full minute before forwarding it to Mia with nothing but “?????”

She called me, laughing so hard she could barely breathe. Then, she did what only a true friend would do—she showed the invoice to her boyfriend, Chris, who sent Eric a counter-invoice, billing him for “wasting a perfectly good evening” of my time. The total? $1,000. Payable in cash or public apology.

Naturally, Eric didn’t take that well. He sent me a series of angry texts calling me “ungrateful” and “manipulative.” That’s when I blocked him.

I’m still not sure what the most absurd part was—his belief that basic kindness needed repayment, the creepy tone of the “collections” warning, or the fact that he genuinely expected a selfie as currency.

As for the little keychain he gifted me that night? I kept it. Not as a memento of romance, but as a hilarious souvenir from the weirdest date of my life.

It’s a reminder that red flags aren’t always visible at dinner—but sometimes, they send you invoices in the morning.