When Eric insisted on paying for our first date, I thought I had met a true gentleman. He arrived with roses, a sweet little gift, and charming conversation. He checked all the boxes. But the next day, when I received a text from him, I expected something cute—a simple “I had a great time” or maybe even an invitation for a second date. Instead, what I got made my stomach drop.
It all started when my best friend, Mia, offered to set me up with someone.
“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, raising an eyebrow. “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 forever.”
That gave me pause. Chris, Mia’s boyfriend, was a great judge of character. If he thought Eric was decent, maybe I should give it a shot.
“Fine,” I sighed. “At least show me a picture.”
A second later, my phone pinged with an image.
The guy in the photo looked good—clean-cut, well-dressed, and sporting a warm smile.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him and set it up. You won’t regret it, I promise.”
After a few casual messages, I agreed to meet Eric for dinner at a nice Italian restaurant by the river. Not too fancy, but a great spot for a first date.
I arrived five minutes early, standing near the entrance, nervously checking my reflection in my phone. Then I spotted him.
He looked just like his photo—maybe even better. He walked with confidence, dressed sharply, and, to my surprise, held a bouquet of roses.
“You must be Kelly,” he said, handing me the flowers with a warm smile. “These are for you.”
“Wow, thank you!” I replied, genuinely touched. “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 tied with a cyan ribbon.
“What’s this?” I asked, eyes widening.
“Just a little something,” he said. “Open it.”
Inside was a sleek silver keychain with the letter “K” engraved on it. It was personalized and thoughtful.
“I asked Mia what you might like,” he added with a proud grin.
I was impressed. Flowers and a gift on a first date? Either he was genuinely interested, or he was the king of first impressions.
The date itself was fantastic. Eric pulled out my chair, listened intently, and asked thoughtful questions about my work as a graphic designer. He remembered details from our texts and made me feel like the most important person in the room.
When the bill came, I instinctively reached for my purse.
“Absolutely not,” Eric said firmly, placing his card down before I could even touch mine. “A man pays on the first date.”
His tone was so final that I didn’t argue.
“Okay, if you insist. Thank you,” I said, thinking he was just being old-fashioned.
As we left, he asked if he could call me again soon.
“I’d like that,” I said truthfully.
He hugged me goodbye—polite but not overbearing—and I drove home with a smile.
The next morning, I woke up to a text from Eric. Expecting a sweet message, I unlocked my phone.
Instead, what I saw nearly made me choke on my coffee.
It was an invoice. A professionally formatted, itemized invoice.
At the top, in bold font:
Date Night Invoice – Amount Due: 1 Outstanding Balance.
My eyebrows shot up as I scrolled down. He had broken down every part of the date into “services rendered.”
- 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
At the bottom, in bold text:
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).
I stared at my screen in shock. My jaw hit the floor. Was this a joke?
I immediately screenshotted it and sent it to Mia.
“OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW,” she texted back.
“Is this real life???” I typed, still in disbelief. “He’s serious about this!”
“Wait till Chris sees this. He’s going to LOSE IT.”
Five minutes later, my phone rang. It was Chris, laughing so hard he could barely speak.
“Kelly… I… I can’t believe this,” he gasped. “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 said. “He’s always been intense about dating, but THIS? This is next-level crazy. Okay, we need to do something about this.”
Chris, the king of pettiness, had an idea.
“I’m making an identical invoice. Same format, fake legal tone, the works.”
An hour later, Chris sent me his masterpiece:
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!
I burst out laughing.
“This is perfect,” I texted him. “Send it!”
“Done,” Chris replied.
Minutes later, Eric’s angry messages flooded my phone.
“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 replying. Instead, I sent a thumbs-up emoji and blocked him.
Mia called that night, still laughing.
“I’m SO sorry,” she said. “I really thought he was normal.”
“Don’t worry,” I said, chuckling. “We all got a great story out of it.”
“True! This is officially being told at every party for the next decade.”
Lesson learned: If a guy insists on paying, make sure he doesn’t send you an invoice after.
The keychain, though? I kept it. Not because it reminded me of Eric, but because it was the best souvenir from the weirdest date of my life.
