When Eric insisted on paying for our first date, I thought I’d found a true gentleman. Roses, a thoughtful gift, charming conversation — he checked every box. I went home smiling, thinking it might’ve been the best first date I’d ever had.
It all started when my best friend, Mia, set us up. She’d never played matchmaker before, but said, “You’ll love him! Total gentleman.” Her boyfriend, Chris, vouched for Eric too, which gave me some confidence. After texting a bit, we agreed to dinner at a riverfront Italian spot.
Eric made quite the entrance — dressed well, flowers in hand, and even brought a custom keychain with my initial. He opened doors, pulled out chairs, asked thoughtful questions, and paid for dinner, saying, “A man pays on the first date,” like it was a rule etched in stone. I was impressed.
The next morning, I expected a sweet follow-up text. Instead, I got… an invoice.
Titled “Date Night Invoice – Amount Due: 1 Outstanding Balance”, it detailed “charges” like:
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Bouquet of Roses: 1 hug
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Custom Keychain: 1 coffee date
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Dinner: A guaranteed second date
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Engaging Conversation: A compliment on his looks
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And so on…
At the bottom:
“Payment expected in full. No refunds. Failure to comply may result in collections (Chris will hear about it).”
I sent it to Mia immediately. “WHAT. THE. HELL.” was her response, followed by Chris calling me, cackling in disbelief. He quickly whipped up a fake counter-invoice:
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Introducing You to a Gorgeous Woman: 1 permanent block
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Pretending to Be a Gentleman: A deep reflection on why you’re still single
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Not Exposing You Online: A generous gift
We sent it to Eric. He didn’t take it well.
“Wow, real mature.”
“You just missed out on a GREAT guy.”
“Chris is a terrible friend.”
I replied with a thumbs-up emoji and blocked him.
Later, Mia apologized, still laughing. “At least we got a story out of it,” I said. And we sure did — one we’ll be telling at parties for years.
Moral of the story? If a guy insists on paying, just make sure he’s not expecting a return on investment.
(And yes, I kept the keychain — it’s a perfect souvenir from the weirdest date of my life.)