When Eric demanded to pay for our first date, I thought I’d met a true nobleman. Roses, a sweet gift, appealing conversation — he was examining all the boxes. When he texted me the next day, I predicted a cute follow-up, but my stomach lowered when I read his message.
My best friend, Mia, meant well when she provided to set me up on a date, but her skills as a matchmaker were totally unproved.
“He’s super nice, Kelly! Total gentleman. You’ll love him,” Mia insisted over the phone while I discovered 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 joyfully. “Plus, Chris vouches for him too. They’ve been friends for ages.”
That gave me pause. Chris, Mia’s boyfriend, was a pretty good judge of character. If he thought this Eric guy was honorable, maybe there was hope.
“Fine,” I sighed. “Show me a picture at least.”
A moment later, my phone tinged an incoming message.
The guy in the photo wasn’t ugly: clean-cut, well-dressed, with a warm smile that attracted his eyes.
“Okay, he’s cute,” I confessed.
“Told you!” Mia informed. “Text him and set it up. You won’t regret it, I promise.”
After a few casual texts, I agreed to encounter Eric for dinner at a new Italian place with a great view of the river. Nothing too interesting, but nice enough for a first date.
I arrived five minutes early and waited near the entrance, like we’d agreed. I was fearfully examining my appearance with my phone camera when I spotted him approaching the restaurant.
My pulse rushed a little. The photo hadn’t lied — he was attractive in that tidy, business-casual way, and he carried himself with confidence.
What I hadn’t predicted was the bouquet of roses in his hand.
Not cheap grocery store flowers, but an actual professional arrangement connected with a ribbon.
“You must be Kelly,” he said. “These are for you.”
“Wow, thank you,” I replied. “You didn’t have to do that.”
“Figured I’d begin the night off right,” he said.
But that wasn’t all.
He extended into his jacket pocket and pulled out a small gift box tied with a cyan bow.
“What’s this?” I asked.
“Just a little something. Open it,” he supported.
Inside was a sleek silver keychain with the letter “K” engraved on it. It was graceful and individualised, something that demanded thought.
“Something just for you,” he said. “I asked Mia what you might like.”
I was honestly impressed. Flowers and a thoughtful gift on a first date? This man was clearly making a statement. Either he was interested, or he was the king of first impressions.
“This is really nice of you,” I said. “Thank you.”
Eric continued his gentlemanly routine without missing a beat. He opened the door, pulled out my chair, and kept steady eye contact throughout our conversation.
“So what made you agree to this setup?” he asked after we’d ordered our meals.
“Mia can be very persuasive,” I laughed. “Plus, she and Chris both vouched for you, which rarely happens.”
“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 poured naturally from there.
We explored shared interests in true crime podcasts and documentaries about strange subcultures.
He told amusing stories about his job as a marketing manager, and I caught myself thinking this might be the best first date I’d ever had.
When the check came, I reached for my purse.
“Absolutely not,” Eric said.
“A man pays on the first date.”
His tone amazed me a little. It wasn’t just gallant, but final, almost like he was reciting an unbreakable rule.
I paused for half a second, then shouted. “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.
He hugged me goodbye (a perfect balance of friendly and interested without being creepy).
The next morning, I woke up to a notification from Eric. My sleepy brain predicted a cute “had a great time” text, but instead, I saw an attachment.
I made coffee and then returned to bed. Curious, I opened it, expecting maybe a photo from the restaurant or something similarly harmless.
At the top, in bold professional typeface:
Date Night Invoice – One Outstanding Balance.
Underneath it was a detailed summary of services provided with associated fees.
At first, I assumed it was a prank, some bizarre attempt at humor that didn’t quite land. But when I read that, my morning coffee almost came back up.
The so-called services he listed were completely absurd, and it made me appreciate his gentlemanly charm in a whole new way.
Rose Bouquet: One Hug
Custom Keychain Gift: one coffee date (arranged within a week)
Opening the car door: A lovely selfie together.
Pulling Out the Chair: Holding hands on the next date.
Engaging Conversation & Active Listening: A complement on my appearance
Full Dinner + Tip Covered: A second date with no excuses.
But the real kicker, the bit that made me realize he’d sent this invoice in earnest, appeared at the bottom in bold text.
Payment is predicted 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’d predicted 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 rapid.
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”
“Is this real life???” I typed back. “He’s serious about this!”
“Wait till Chris sees this. He’s going to LOSE IT,” she answered.
Five minutes later, my phone rang.
It was Chris, and he was bawling with laughter.
“Kelly, I can’t believe this,” he answered. “I’ve known this dude for years and never, not once, did I think he’d pull something this insane.”
“So, this isn’t a joke?” I asked.
“No way,” Chris replied. “Eric’s always been a bit… intense about dating, but this is next level. Okay, we need to get back at this dude.”
Chris was the mastermind of next-level pettiness.
Instead of just roasting Eric in their group chat, he planned to take it up a notch.
“I’m making an identical invoice,” he announced. “Same formatting, fake legal tone, ridiculous charges, the works.”
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 a moment later.
Not long afterward, my phone drunk a series of progressively 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 bother engaging. What was there to say to someone who thought human connection worked on a transaction basis? I just sent him a thumbs-up emoji and blocked his number.
Mia called me later that night, still giggling about the entire thing.
“I’m very sorry,” she said. “I honestly thought he was normal. Chris didn’t realize he was like this either.”
“Don’t worry about it,” I said, surprising myself with how relaxed I felt. “We all got a great story out of it, at least.”
“True,” she agreed. “This is officially going to be told at every party for the next decade.”
The whole event taught me one golden rule about dating: if a guy insists on paying, make sure he doesn’t send you an invoice later.
What about the keychain, though? I kept it. Not because it reminded me of Eric, but because it was a humorous memento from the most unusual date of my life.
