When Eric insisted on paying for our first date, I honestly thought I’d found a real gentleman. He brought roses, gave me a sweet gift, and carried on the most charming conversation. He was ticking every box. So, when he texted me the next morning, I expected something cute like, “I had a great time.” Instead, what I got made my stomach drop.
Let me back up.
My best friend Mia meant well when she offered to set me up on a blind date. But to be fair, her matchmaking skills had never been tested before.
“He’s super nice, Kelly! Total gentleman. You’ll love him,” Mia said excitedly over the phone while I was knee-deep in my closet trying to find something decent to wear.
“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,” she said confidently. “And Chris vouches for him too. They’ve been friends since college.”
That gave me pause. Chris—Mia’s boyfriend—was a solid guy. If he thought this Eric guy was good news, maybe I could give it a shot.
“Fine,” I sighed. “Show me a picture at least.”
Ping. A photo popped up on my phone.
The guy looked decent. Clean-cut, dressed well, and he had one of those smiles that made you feel warm just looking at it.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it, I promise.”
So, I did. After a few messages back and forth, we agreed to have dinner at a trendy new Italian place with a lovely view of the river. It was nice—not over-the-top, but perfect for a first date.
I arrived five minutes early and stood by the entrance, checking my lipstick in my phone camera. That’s when I saw him walking up.
He looked exactly like his picture—maybe even better in person. Confident, polished, and carrying… wait, was that a bouquet of roses?
Not your average grocery store flowers either. These were professional, ribbon-tied, and beautifully arranged.
“You must be Kelly,” he said with that same warm smile from the photo. “These are for you.”
“Wow, thank you,” I said, genuinely surprised. “You didn’t have to do that.”
“Figured I’d start the night off right,” he said smoothly.
Then he reached into his jacket pocket and pulled out a small gift box wrapped with a pretty cyan bow.
“What’s this?” I asked, raising my eyebrows.
“Just a little something. Open it,” he encouraged.
Inside was a shiny silver keychain with the letter “K” engraved on it. It was simple, elegant, and clearly chosen with care.
“I asked Mia what you might like,” he added casually.
I was honestly impressed. This guy came prepared. Flowers and a thoughtful gift? Either he was serious about me… or this was the most calculated charm offensive I’d ever seen.
“This is really sweet,” I said. “Thank you.”
From there, the gentleman act continued. He opened every door, pulled out my chair, and listened—really listened—while we talked.
He asked about my job as a graphic designer and remembered details I’d only mentioned in passing while texting.
“So, what made you say yes to a blind date?” he asked once we ordered.
“Mia can be pushy,” I laughed. “And both she and Chris said you were worth meeting. That’s rare.”
“They’re a great couple,” he nodded. “Chris is like a brother. We met in college. He’s always been honest and loyal.”
We laughed and bonded over our shared love for true crime podcasts and weird documentaries. He told funny stories about his job as a marketing manager. Honestly, it was one of the best first dates I’d ever had.
When the check came, I instinctively reached for my purse.
“Absolutely not,” Eric said firmly, sliding his card onto the tray before I even got my wallet open. “A man pays on the first date.”
There was something about his tone—like it wasn’t just politeness but some ancient rule passed down from his ancestors. Still, I shrugged.
“Okay, if you insist. Thank you.”
Outside, he asked if he could call me again.
“I’d like that,” I said with a smile.
He gave me a hug—just the right mix of warm and respectful—and I drove home thinking, That went… really well.
The next morning, my phone buzzed with a message from Eric. Still sleepy, I expected something like, “Had an amazing time!”
Instead, I saw an attachment.
Curious, I opened it while sipping my coffee—and almost choked.
It was an invoice. A real one. Professionally formatted, bold letters at the top:
Date Night Invoice – Amount Due: 1 Outstanding Balance
My eyes scanned down the list—and my jaw dropped.
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 at the bottom, it said:
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 was stunned. I mean… what?!
It would’ve been creepy if he asked for money. But asking for affection like it was a business transaction? That was next-level bizarre.
I immediately sent a screenshot to Mia.
Her reply came lightning fast:
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
I texted:
“Is this real life???”
“Wait till Chris sees this. He’s going to LOSE IT.”
And he did. Five minutes later, my phone rang.
Chris was laughing so hard he could barely breathe.
“Kelly,” he said, wheezing, “I’ve known this dude forever. I swear I had no idea he was capable of something this unhinged!”
“So… he’s serious?” I asked.
“Dead serious,” Chris replied. “He’s always been kind of intense about dating, but this? This is insane.”
Then Chris had an idea.
“I’m making a revenge invoice,” he announced. “Same layout. Same tone. But this one’s going to be legendary.”
One hour later, he sent it.
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 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 Chris. “Send it!”
“Already did,” he replied.
And sure enough, a storm of messages from Eric followed.
“Wow, real mature.”
“I was just setting realistic expectations. Not everyone’s rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t even respond. I just sent a thumbs-up emoji and blocked him.
Later that night, Mia called, still laughing.
“I’m SO sorry,” she said between giggles. “I swear he seemed normal.”
“Honestly? I’m not mad,” I said. “This might be the funniest dating story I’ll ever have.”
“It’s going in the party story hall of fame,” Mia promised. “Forever.”
And it did. It’s now one of those stories that gets told whenever someone brings up bad dates. But I learned a lesson that day:
If a guy insists on paying… double-check he’s not planning to invoice you later.
Oh, and the keychain? I kept it. Not because it reminded me of Eric, but because it’s a hilarious souvenir from the weirdest date I’ve ever had.
