When Eric insisted on covering the cost of our first date, I thought I’d met a true gentleman. Roses, a thoughtful gift, charming conversation — he was ticking all the boxes. So when he texted me the next day, I expected a cute follow-up, but my stomach dropped when I read his message.
My best friend, Mia, had meant well when she set me up on the date, but her matchmaking skills were untested.
“He’s super nice, Kelly! A total gentleman. You’ll love him,” Mia had told me 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,” she replied confidently. “And Chris vouches for him too. They’ve been friends for ages.”
That gave me pause. Chris, Mia’s boyfriend, had a pretty good judge of character. If he thought Eric was decent, maybe there was hope.
“Fine,” I sighed. “Show me a picture at least.”
A moment later, my phone pinged with a message.
The guy in the photo looked decent: clean-cut, well-dressed, and smiling with genuine warmth.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it, I promise.”
After some casual texts, I agreed to meet Eric at a new Italian place by the river. Nothing too fancy, but nice for a first date.
I arrived five minutes early and waited by the entrance. As I was checking my appearance with my phone camera, I saw him walking toward the restaurant.
My pulse quickened. The photo hadn’t lied — he was attractive in a clean-cut, business-casual way and carried himself confidently.
But I didn’t expect him to have a bouquet of roses in hand.
Not the cheap grocery store kind, but a professional arrangement tied with a ribbon.
“You must be Kelly,” he said, flashing the same warm smile from his photo. “These are for you.”
“Wow, thank you,” I said, genuinely surprised as I accepted the flowers. “You didn’t have to do that.”
“Figured I’d start the night off right,” he said as he handed 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 ribbon.
“What’s this?” I asked, my eyebrows raised in surprise.
“Just a little something. Open it,” he said with a grin.
Inside was a sleek silver keychain with a “K” engraved on it. It was tasteful and personal — clearly well thought out.
“Something just for you,” he said smoothly. “I asked Mia what you might like.”
I was impressed. Flowers and a thoughtful gift on a first date? This guy was either extremely interested or the king of first impressions.
“This is really nice of you,” I said, touched. “Thank you.”
Eric kept up his gentlemanly act flawlessly. He opened the door for me, pulled out my chair, and maintained steady eye contact as we talked.
He asked thoughtful questions about my job as a graphic designer, remembered little details about my family that I’d casually mentioned in texts, and made me feel like I was the most interesting person in the room.
“So, what made you agree to this setup?” he asked after our meals had arrived.
“Mia can be very persuasive,” I laughed. “Plus, she and Chris both vouched for you, which is rare.”
“They’re a great couple,” he said. “Chris and I go way back to college. He’s always been a stand-up guy.”
The conversation flowed easily from there.
We discovered shared interests in true crime podcasts and documentaries about odd subcultures.
He told funny stories about his job in marketing, and I found myself thinking that this might be the best first date I’d ever had.
When the check came, I reached for my purse.
“Absolutely not,” Eric said firmly, placing his card on the check presenter before I could even open my purse. “A man pays on the first date.”
His tone caught me off guard. It wasn’t just polite — it was final, like a rule he couldn’t break.
I paused for a second, then shrugged. “Okay, if you insist. Thank you.”
I wasn’t about to argue over a free meal, especially after such a pleasant evening. We walked out together, and he asked if he could call me again soon.
“I’d like that,” I replied, and meant it.
He hugged me goodbye (a perfect mix of friendly and interested without being creepy). I drove home with a smile, thinking that had been one of the best first dates I’d ever been on.
The next morning, I woke up to a message from Eric. I expected a simple “had a great time” text, but instead, I saw an attachment.
I made coffee and then went back to bed. Curious, I opened the message, expecting maybe a photo from the restaurant or something innocent.
It was an invoice. A professionally formatted, detailed invoice.
At the top, in bold font, it read:
Date Night Invoice – Amount Due: 1 Outstanding Balance.
Underneath, there was a full breakdown of “services rendered” with attached charges:
- 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 my looks
- Full Dinner + Tip Covered: A second date, no excuses
But the real kicker was at the bottom in bold:
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.
It would’ve been bad enough if he was just expecting monetary compensation, but charging me with required affection and attention? Who does that?
I screenshot the invoice immediately and sent it to Mia. Her response was instant:
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
“Is this real life???” I texted back in disbelief. “He’s serious!”
“Wait till Chris sees this. He’s going to LOSE IT,” she replied.
Five minutes later, my phone rang.
It was Chris, and he was laughing hysterically.
“Kelly, I can’t believe this,” he gasped between fits of laughter. “I’ve known this guy for years, and never did I think he’d pull something like this.”
“So this isn’t a joke?” I asked.
“No way,” Chris said. “Eric’s always been a bit… intense about dating, but this is next-level. We need to get back at him.”
Chris, the king of petty revenge, had a plan.
“I’m making an identical invoice,” he declared. “Same formatting, fake legal tone, ridiculous charges, the whole works.”
An hour later, Chris sent me his masterpiece.
It listed charges like:
- 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!”
“Forwarded!” He replied.
Soon after, my phone lit up with a series of increasingly angry messages from Eric:
- “Wow, 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 even bother replying. What could I say to someone who treated human connections like a business transaction? I simply sent him a thumbs-up emoji and blocked his number.
Mia called me later, still laughing.
“I’m so sorry,” she said. “I thought he was normal. Chris didn’t know either.”
“Don’t worry about it,” I said, surprising myself with how unbothered I felt. “We all got a great story out of it.”
“True,” Mia agreed. “This will be told at every party for the next decade.”
The whole experience taught me one valuable lesson for dating: if a guy insists on paying, make sure he’s not going to send you an invoice afterward.
As for the keychain? I kept it, not as a reminder of Eric, but as a hilarious memento from the weirdest date of my life.