When Eric insisted on paying for our first date, I thought I had met a true gentleman. He brought roses, gave me a thoughtful gift, and held the most charming conversation. He was checking all the right boxes. But when he texted me the next day, I expected a sweet follow-up. Instead, my stomach dropped as I read his message.
My best friend, Mia, had meant well when she offered to set me up. But her matchmaking skills? Completely untested.
“He’s super nice, Kelly! A total gentleman. You’ll love him,” Mia gushed over the phone while I rummaged 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. “Plus, Chris vouches for him. They’ve been friends for ages.”
That made me pause. Chris, Mia’s boyfriend, was a solid judge of character. If he thought Eric was decent, maybe this wouldn’t be so bad.
“Fine,” I sighed. “At least show me a picture.”
A second later, my phone pinged. I opened the message and saw a photo of Eric—clean-cut, well-dressed, with a warm smile that reached his eyes.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it.”
After exchanging a few messages, Eric and I planned to meet at a new Italian restaurant by the river. It wasn’t overly fancy, but nice enough for a first date.
I arrived five minutes early, anxiously checking my reflection in my phone camera. That’s when I spotted him approaching the restaurant, and my pulse quickened. The picture hadn’t lied—he was attractive in that business-casual way, and he carried himself with confidence.
What I didn’t expect? The bouquet of roses in his hand.
Not cheap grocery store flowers, but an elegant arrangement tied with a ribbon.
“You must be Kelly,” he said, smiling warmly. “These are for you.”
“Wow, thank you,” I replied, taking the flowers. “You didn’t have to do that.”
“Just wanted to start the night off right,” he said smoothly.
Then, he pulled out a small gift box wrapped with a cyan bow.
“What’s this?” I asked, my eyebrows raising in surprise.
“Just a little something. Open it.”
Inside was a sleek silver keychain with the letter “K” engraved on it.
“I asked Mia what you might like,” he added with a wink.
I was genuinely impressed. Flowers and a personalized gift on a first date? This guy was either really interested or the king of first impressions.
“This is really thoughtful,” I admitted. “Thank you.”
The gentleman routine continued. He opened doors, pulled out my chair, and maintained steady eye contact during our conversation. He asked thoughtful questions, remembered small details I had mentioned in texts, and made me feel like the most interesting person in the room.
“So what made you agree to this setup?” he asked as we ordered.
“Mia can be very persuasive,” I laughed. “And Chris vouched for you, which rarely happens.”
“They’re a great couple,” he nodded. “Chris and I go way back. He’s always been a stand-up guy.”
We discovered we both loved true crime podcasts and bizarre documentaries. He shared funny stories about his job as a marketing manager, and I caught myself thinking—this might be the best first date I’ve ever had.
When the check came, I reached for my purse.
“Absolutely not,” Eric said firmly, placing his card down before I could even react. “A man pays on the first date.”
His tone was so final, almost like he was reciting a rule set in stone.
I hesitated but shrugged. “Okay, if you insist. Thank you.”
We left the restaurant together, and he asked if he could call me soon.
“I’d like that,” I said truthfully.
He hugged me goodbye—not too much, not too little. Just right.
I drove home smiling. This was easily one of the best first dates I had ever been on.
The next morning, my phone buzzed. It was Eric.
Sleepily, I expected a cute “had a great time” message. Instead, I saw an attachment.
I made coffee, crawled back into bed, and opened it.
It was an invoice.
A professionally formatted, detailed invoice.
At the top, in bold letters:
DATE NIGHT INVOICE – AMOUNT DUE: 1 OUTSTANDING BALANCE
Below that was a full breakdown of “services rendered” and “expected payments.”
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 cherry on top?
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 nearly choked on my coffee.
Was this a joke? I reread it, hoping I had misunderstood. But no. Eric had actually itemized our date, expecting repayment in the form of affection and commitment.
I screenshot the invoice 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 typed. “He’s serious about this!”
“Wait till Chris sees this. He’s going to LOSE IT.”
Five minutes later, my phone rang.
Chris was laughing so hard he could barely speak.
“Kelly, I can’t believe this. I’ve known this guy for YEARS and never thought he’d pull something this crazy!”
“So this isn’t a joke?” I asked.
“No way,” Chris confirmed. “Eric’s always been… intense about dating, but this is next level. Okay, we need to get back at him.”
Chris crafted an identical invoice—same format, fake legal language, absurd charges.
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: A formal apology to all women you’ve dated before
Not Exposing You to the Internet: A generous gift you should be grateful for
Payment due IMMEDIATELY. Failure to comply may result in public humiliation. Cheers!
“This is perfect,” I texted. “Send it!”
Moments later, Eric’s messages flooded in.
“Wow, really mature.”
“I was just trying to set expectations. Not everyone is rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I replied with a thumbs-up emoji and blocked him.
Later that night, Mia called, still laughing.
“I’m so sorry,” she said. “I really thought he was normal.”
“Don’t worry,” I said, grinning. “At least we got a great story.”
One thing was for sure—if a guy insists on paying, make sure he’s not going to send you an invoice afterward.
