When Eric insisted on paying for our first date, I thought I had met a true gentleman. The bouquet of roses, the sweet little gift, his charming conversation—he seemed like the perfect guy. But the next morning, when I opened his message, my stomach dropped. Instead of a cute follow-up text, he had sent me an invoice.
It all started when my best friend, Mia, decided to play matchmaker.
“Kelly, trust me, he’s a total gentleman! You’ll love him,” she gushed over the phone while I flipped through my closet.
“You’ve never set me up before. What makes you think you know my type?” I asked skeptically.
“Because I know you better than anyone! And Chris vouches for him too. They’ve been friends forever.”
That gave me pause. Chris, Mia’s boyfriend, was a good judge of character. If he approved of this Eric guy, maybe he was worth a shot.
“Fine,” I sighed. “At least show me a picture.”
A moment later, my phone pinged. I opened the message and studied the guy in the photo. Clean-cut, well-dressed, with a warm smile. Not bad.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it!”
After some casual back-and-forth, Eric and I agreed to meet for dinner at a nice Italian place by the river. It wasn’t over-the-top fancy, but it had a beautiful view and a cozy atmosphere—perfect for a first date.
I arrived five minutes early and waited near the entrance, pretending to check my phone. When I spotted Eric walking toward me, my heart picked up a little. The photo hadn’t lied—he was handsome, confident, and well-dressed.
Then I saw the bouquet of roses in his hands.
Not just a few flowers from the grocery store, but an elegant, professionally arranged bouquet tied with a ribbon.
“You must be Kelly,” he said, smiling as he handed me the flowers. “These are for you.”
“Wow, thank you! You really didn’t have to do this,” I said, genuinely touched.
“Figured I’d start the night off right,” he replied smoothly. But he wasn’t done yet.
He reached into his jacket pocket and pulled out a small gift box wrapped with a blue bow.
“What’s this?” I asked, raising an eyebrow.
“Just a little something,” he said. “Open it.”
Inside was a sleek silver keychain with the letter “K” engraved on it. It was simple, elegant—thoughtful.
“Something just for you,” he added. “I asked Mia what you might like.”
I was impressed. A man bringing flowers and a personalized gift on a first date? Either he was really interested, or he was the king of first impressions.
“That’s really sweet,” I said. “Thank you.”
Throughout dinner, he continued his gentlemanly act—pulling out my chair, maintaining eye contact, and asking thoughtful questions about my job as a graphic designer. He even remembered small details from our texts, like the fact that my younger brother was studying abroad.
“So, what made you agree to this setup?” he asked as we waited for our food.
“Mia can be very persuasive,” I laughed. “And since both she and Chris vouched for you, I figured why not?”
“They’re a great couple,” he nodded. “Chris and I go way back to college. He’s always been a stand-up guy.”
The conversation flowed naturally. We both loved true crime podcasts, quirky documentaries, and Italian food. Eric told funny stories about his job as a marketing manager, and I found myself genuinely enjoying the evening.
Then the check arrived.
I reached for my purse, but Eric was faster.
“Absolutely not,” he said firmly, placing his card on top of the bill before I could even unzip my wallet. “A man pays on the first date.”
His tone caught me off guard. It wasn’t just polite—it was final, like a rule written in stone.
“Okay, if you insist. Thank you,” I said, not wanting to argue over a free meal.
Afterward, he walked me to my car and asked if he could call me again soon.
“I’d like that,” I replied honestly. He gave me a friendly, non-creepy hug, and I drove home smiling, thinking it was one of the best first dates I’d ever had.
Then the next morning happened.
I woke up to a message from Eric. Expecting a cute “I had a great time” text, I opened it and nearly spit out my coffee.
It was an invoice.
A professionally formatted, detailed invoice.
At the top, in bold letters: Date Night Invoice – Amount Due: 1 Outstanding Balance.
Below that, a full breakdown of “services rendered”:
- Bouquet of Roses: 1 hug
- Custom Keychain Gift: 1 coffee date within a week
- Opening Car Door: A cute selfie together
- Pulling Out Chair: Holding hands on the next date
- Engaging Conversation & Active Listening: A compliment about his looks
- Full Dinner + Tip Covered: A second date—no excuses
But the best part was the final line:
Payment is expected in full. No refunds. Failure to comply may result in an outstanding balance being sent to collections (Chris will hear about it). Looking forward to your prompt payment!
My jaw hit the floor.
I immediately screenshotted it and sent it to Mia.
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
“Is this real life???” I texted back. “He’s serious about this!”
“Wait till Chris sees this. He’s going to LOSE IT.”
Five minutes later, my phone rang. It was Chris, laughing so hard he could barely breathe.
“Kelly, I can’t believe this,” he gasped. “I’ve known this dude for years and NEVER thought he’d pull something this insane.”
“So, this isn’t a joke?” I asked.
“No way,” Chris confirmed. “He’s always been weird about dating, but THIS is next level.”
Chris, being the master of pettiness, had an idea.
“I’m sending him an invoice back,” he declared. “Same format, same ridiculous tone.”
An hour later, he sent me his masterpiece:
Service Invoice – Amount Due: A Lifetime of Silence
- Introducing You to a Gorgeous Woman: 1 permanent block on all platforms
- Convincing Her You Were a Gentleman: A deep, personal reflection on why you’re single
- Letting You Sit at the Same Table as Her: A formal apology to all women you’ve dated
- Not Exposing You to the Internet: A generous gift you should be grateful for
Payment is due IMMEDIATELY. Failure to comply may result in public humiliation. Cheers!
I nearly fell off my bed laughing. “Send it!” I texted him.
Seconds later, Eric’s response came flooding in:
“Wow, really mature.”
“I was just trying to set realistic expectations.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t reply. Just sent a thumbs-up emoji and blocked his number.
Later that night, Mia called me, still giggling.
“I’m SO sorry,” she said. “I really thought he was normal.”
“Don’t worry. At least we got a great story out of it.”
And a new rule for dating: If a guy insists on paying, make sure he’s not planning to send you an invoice later.
The keychain, though? I kept it. A hilarious souvenir from the weirdest date of my life.
