When Eric insisted on paying for our first date, I thought I’d met a true gentleman. Roses, a sweet gift, charming conversation—he was checking all the boxes. But when he texted me the next day, I had no idea I was about to be hit with something far more bizarre than I could’ve ever imagined.
My best friend, Mia, had good intentions when she offered to set me up. “He’s super nice, Kelly! Total gentleman. You’ll love him!” she said over the phone while I searched through my closet.
“You’ve never set me up before,” I reminded her. “What makes you think you know my type?”
“Because I know you better than anyone,” Mia replied confidently. “Plus, Chris vouches for him too. They’ve been friends forever.”
Chris was Mia’s boyfriend, and I trusted his judgment. If he thought Eric was decent, maybe there was hope.
“Fine,” I sighed. “Show me a picture.”
Moments later, my phone pinged. The guy in the photo wasn’t bad looking: clean-cut, well-dressed, with a warm smile. Okay, he was cute.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it, I promise.”
A few casual texts later, I agreed to meet Eric for dinner at a trendy Italian place with a view of the river. Nothing too fancy—just a nice first date spot.
I arrived five minutes early, waiting near the entrance. I was checking my appearance on my phone when I spotted him. Eric walked toward me with confidence, a bouquet of roses in hand.
“You must be Kelly,” he said, flashing the same warm smile from the photo. “These are for you.”
“Wow, thank you,” I said, genuinely surprised. “You didn’t have to do that.”
“I figured I’d start the night off right,” he replied, handing me the bouquet.
But that wasn’t all. He reached into his jacket pocket and pulled out a small gift box tied with a cyan bow.
“What’s this?” I asked, eyebrows raised.
“Just a little something. Open it,” he said.
Inside was a sleek silver keychain with the letter “K” engraved on it. Thoughtful and personalized. It was a nice touch.
“Something just for you,” he said smoothly. “I asked Mia what you might like.”
Impressed, I smiled. Flowers, a thoughtful gift—he was definitely making an impression.
Eric continued his gentlemanly routine, opening the door for me, pulling out my chair, maintaining steady eye contact. He asked about my job as a graphic designer, remembered little details from our texts, and made me feel like the most interesting person in the room.
“So, what made you agree to this setup?” he asked after we ordered.
“Mia can be very persuasive,” I laughed. “Plus, she and Chris both vouched for you.”
“They’re a great couple,” Eric said. “Chris and I go way back to college. He’s always been a stand-up guy.”
The evening continued with easy conversation, sharing interests in true crime podcasts and strange documentaries. It was, without a doubt, one of the best first dates I’d ever had.
When the check came, I reached for my purse, but Eric was quick to stop me.
“Absolutely not,” he said firmly, putting his card down before I could open my purse. “A man pays on the first date.”
I paused, slightly taken aback, but shrugged. “Okay, if you insist. Thank you.”
We walked out together, and Eric asked if he could call me again soon. “I’d like that,” I replied, genuinely meaning it.
He hugged me goodbye—a perfect balance of friendly and interested. I drove home smiling, thinking this had been an amazing first date.
The next morning, I woke up to a text from Eric. I was expecting a cute follow-up message, but instead, my stomach dropped when I opened it.
It was an invoice.
A professionally formatted invoice with the title:
Date Night Invoice – Amount Due: 1 Outstanding Balance
I stared at the screen, blinking, expecting a joke. But no—there it was, a detailed breakdown of “services rendered.”
- Bouquet of Roses: 1 hug
- Custom Keychain Gift: 1 coffee date (scheduled within one week)
- Opening Car Door: A cute selfie together
- Pulling Out Chair: Holding hands on the next date
- Engaging Conversation & Active Listening: A compliment about my looks
- Full Dinner + Tip Covered: A second date, no excuses
And the kicker? A warning at the bottom in bold, ominous text:
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!
I couldn’t believe it. My first thought? It had to be a joke. But as I read through it again, I realized he was serious.
I screenshot the invoice and sent it to Mia. Her response came almost immediately:
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
“Is this real life???” I typed back. “He’s serious about this!”
“Wait until Chris sees this. He’s going to LOSE IT,” Mia replied.
Five minutes later, my phone rang. It was Chris, barely able to speak between fits of laughter.
“Kelly, I can’t believe this. I’ve known this dude for years and never thought he’d do something like this.”
“So this isn’t a joke?” I asked.
“No way,” Chris confirmed. “Eric’s always been a little intense about dating, but this? Next level. We’ve got to get back at him.”
Chris, being the mastermind of next-level pettiness, had a plan.
“I’m making an identical invoice,” he declared. “Same formatting, fake legal tone, ridiculous charges.”
An hour later, Chris sent me his creation. It was pure genius:
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 before
- Not Exposing You to the Entire Internet: A generous gift you should be grateful for
Payment is due IMMEDIATELY. Failure to comply may result in public humiliation. Cheers!
“This is perfect,” I texted him. “Send it!”
A few minutes later, I started getting increasingly angry messages from Eric.
“Really mature.”
“I was just trying to set realistic expectations; not everyone is rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t bother engaging. Instead, I sent a simple thumbs-up emoji and blocked his number.
Mia called me that night, still laughing.
“I’m so sorry,” she said. “I really thought he was normal. Chris had no idea either.”
“Don’t worry about it,” I replied, surprising myself with how unbothered I felt. “We got a great story out of it, at least.”
Mia agreed. “True. This is going to be told at every party for the next decade.”
As for me? I learned a golden rule for dating: If a guy insists on paying, make sure he’s not going to send you an invoice afterward.
And the keychain? I kept it. Not as a reminder of Eric, but because it was the funniest souvenir from the weirdest date of my life.
