He brought roses, a sweet little gift, and carried himself with such charm — he seemed to be ticking all the right boxes. So, when he texted me the next day, I expected a sweet follow-up message. Instead, my stomach dropped as soon as I read what he sent.
My best friend, Mia, had meant well when she offered to set me up, but she’d never played matchmaker before, so I wasn’t entirely sure about her skills.
“He’s really nice, Kelly! Such a gentleman. You’re going to like him,” Mia assured me over the phone as I rifled 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 said confidently. “Plus, Chris vouches for him too. They’ve been friends for years.”
That made me pause. Chris — Mia’s boyfriend — was someone I trusted to read people well. If he thought Eric was decent, maybe there was something there.
“Alright,” I finally said with a sigh. “At least send me a picture.”
A moment later, my phone buzzed with a new message.
The man in the photo wasn’t bad looking — clean-cut, nicely dressed, with a warm smile that reached his eyes.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and make plans. Trust me, you won’t regret it.”
After a bit of casual texting, I agreed to meet Eric for dinner at a new Italian restaurant with a beautiful view of the river. It wasn’t overly fancy but nice enough for a first date.
I got there about five minutes early and stood by the entrance, just like we’d planned. I was nervously checking my reflection in my phone’s camera when I spotted him walking toward the restaurant.
My pulse picked up. The photo hadn’t been misleading — he was just as attractive in person, with that business-casual, confident vibe.
What I hadn’t anticipated, though, was the bouquet of roses in his hand.
These weren’t the cheap kind you grab at the grocery store — this was a florist’s arrangement, tied neatly with a ribbon.
“You must be Kelly,” he said with that same warm smile. “These are for you.”
“Wow, thank you,” I replied, genuinely surprised as I took them. “You didn’t have to do that.”
“Figured I’d start the night off right,” he said, handing me the flowers.
But that wasn’t all.
He reached into his jacket pocket and pulled out a small gift box tied with a bright cyan ribbon.
“What’s this?” I asked, my eyebrows shooting up.
“Just a little something. Go ahead and open it,” he encouraged.
Inside was a sleek silver keychain with the letter “K” engraved on it. It was simple, personal, and clearly 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 man was clearly trying to make an impression. Either he was genuinely interested, or he was the undisputed king of first-date gestures.
“This is really sweet of you,” I said sincerely. “Thank you.”
Throughout dinner, Eric stayed in full gentleman mode. He opened the door for me, pulled out my chair, and kept steady, engaged eye contact.
He asked me thoughtful questions about my work as a graphic designer, remembered little details about my family I’d mentioned over text, and made me feel like the most interesting person in the restaurant.
“So, what made you say yes to this setup?” he asked after we ordered.
“Mia can be pretty convincing,” I said with a laugh. “And both she and Chris vouched for you, which doesn’t happen often.”
“They’re a great couple,” he agreed. “Chris and I go back to college. He’s always been a stand-up guy.”
The conversation flowed so naturally.
We found out we both loved true crime podcasts and quirky documentaries about odd subcultures.
He told me some funny stories about his job in marketing, and I caught myself thinking this might actually be the best first date I’d ever had.
When the bill came, I reached for my purse.
“Absolutely not,” Eric said firmly, slipping his card onto the check before I could even open my wallet. “A man always pays on the first date.”
His tone wasn’t just polite — it was final, almost like it was some unbreakable code.
I hesitated for a moment, then shrugged. “Alright, if you insist. Thank you.”
I wasn’t going to argue about a free meal after such a lovely evening. As we left, he asked if he could call me again.
“I’d like that,” I replied honestly.
He hugged me goodbye — warm and respectful — and I drove home smiling, thinking this might have been one of the best first dates of my life.
The next morning, I woke up to a notification from Eric. Half asleep, I expected a cute “had a great time” message. Instead, there was an attachment.
I grabbed a coffee and sat back down, curious. I figured it was maybe a photo from dinner or something harmless.
It wasn’t.
It was an invoice — professionally formatted, complete with bold headings and itemized details.
At the top, in big letters:
Date Night Invoice – Amount Due: 1 Outstanding Balance
Below was a breakdown of “services” and the “payment” he expected in return.
At first, I thought it was some bizarre attempt at humor. But the more I read, the more my coffee threatened to come back up.
Bouquet of Roses: 1 hug
Custom Keychain: 1 coffee date within a week
Opening Car Door: A cute selfie together
Pulling Out Chair: Holding hands next time
Engaging Conversation: A compliment about his looks
Full Dinner + Tip: A guaranteed second date
And at the bottom, in bold:
Payment expected in full. No refunds. Failure to comply may result in the balance being sent to collections (Chris will hear about it). Looking forward to your prompt payment!
My jaw dropped.
It was bad enough if he’d expected money — but this was worse. He was charging me in affection and attention like we were in some bizarre dating contract.
I took a screenshot and sent it to Mia immediately.
Her response was instant: “OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
“This is real??” I typed back, still stunned.
“Just wait. Chris is going to lose it,” she replied.
Five minutes later, Chris called, laughing so hard he could barely breathe.
“I’ve known this guy for years, Kelly, and never once did I think he’d pull something this crazy,” he said between gasps.
“So, this isn’t a joke?” I asked.
“Nope,” Chris said. “Eric’s always been… intense about dating, but this? This is wild. We need to get him back.”
Chris was the king of petty comebacks.
Instead of just mocking Eric in the group chat, he decided to hit him with his own invoice — identical format, same over-the-top tone, but with charges for putting me through the experience.
An hour later, he sent me the masterpiece:
Service Invoice – Amount Due: A Lifetime of Silence
Introducing You to a Gorgeous Woman: Permanent block on all platforms
Convincing Her You Were a Gentleman: A deep reflection on why you’re single
Letting You Sit at the Same Table as Her: Formal apology to every woman you’ve ever dated
Not Exposing You Online: A gift you should be eternally grateful for
Payment due immediately. Failure to comply will result in public humiliation. Cheers!
“This is perfect,” I told him.
“Already sent it,” Chris replied.
Not long after, my phone blew up with angry messages from Eric.
“Wow, really mature.”
“I was just setting expectations. Not everyone’s rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t bother responding beyond a simple thumbs-up emoji before blocking his number.
Later that night, Mia called, still laughing.
“I’m so sorry,” she said. “I thought he was normal. Chris didn’t see this coming either.”
“Don’t worry,” I told her. “If nothing else, we got a hilarious story out of it.”
“True,” she agreed. “This is going to be retold at every party for years.”
Now, I have a new dating rule: if a guy insists on paying, make sure he’s not planning to send you a bill later.
The keychain? I kept it — not as a reminder of Eric, but as the funniest souvenir from the weirdest date I’ve ever been on.