When Eric insisted on paying for our first date, I thought I had met a true gentleman. The roses, the thoughtful gift, the charming conversation—he was checking all the right boxes. But the next day, when I received his text, my stomach dropped.
My best friend, Mia, had meant well when she decided to set me up. But her matchmaking skills? Completely untested.
“He’s super nice, Kelly! Total gentleman. You’ll love him,” she gushed over the phone while I rummaged through my closet.
“You’ve never set me up before,” I reminded her. “How do you know he’s my type?”
“Because I know you better than anyone,” she replied confidently. “And Chris vouches for him! They’ve been friends forever.”
That gave me pause. Chris, Mia’s boyfriend, was a solid judge of character. If he thought Eric was a good guy, maybe this wasn’t the worst idea.
“Fine,” I sighed. “At least show me a picture.”
A moment later, my phone pinged.
The guy in the photo wasn’t bad-looking—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 a few friendly messages, Eric and I agreed to meet at a nice Italian restaurant by the river. It wasn’t overly fancy, but definitely a great spot for a first date.
I arrived five minutes early and stood near the entrance, anxiously checking my reflection on my phone. Then, I saw him approaching.
My pulse quickened. The picture hadn’t lied—he was attractive and carried himself with confidence. But what I hadn’t expected was the bouquet of roses in his hands.
Not some last-minute grocery store flowers. No, this was a professional arrangement, tied with a ribbon.
“You must be Kelly,” he said, flashing that same warm smile. “These are for you.”
“Wow, thank you,” I said, genuinely surprised. “You really didn’t have to.”
“Wanted to start the night off right,” he said smoothly, handing them to me.
Then, he reached into his jacket pocket and pulled out a small gift box, tied with a cyan bow.
“What’s this?” I asked, raising an eyebrow.
“Just a little something. Open it,” he encouraged.
Inside was a sleek silver keychain with the letter “K” engraved on it. Thoughtful. Personalized. Definitely not something bought last-minute.
“Something just for you,” he said proudly. “I asked Mia what you might like.”
I was impressed. A man putting in this much effort on a first date? Either he was really interested, or he was an expert at first impressions.
“That’s really sweet,” I said, genuinely touched. “Thank you.”
The night continued with his gentlemanly gestures. He opened the restaurant door, pulled out my chair, and kept steady eye contact throughout dinner. He asked thoughtful questions about my job, remembered details I’d barely mentioned in texts, and made me feel like the most fascinating person in the room.
“So, what made you agree to this setup?” he asked as we waited for our food.
“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 flowed effortlessly. We discovered a mutual love for true crime podcasts and bizarre documentaries. He shared funny stories from his marketing job, and honestly? It was shaping up to be one of the best first dates I’d ever had.
Then the check arrived.
I reached for my purse, but Eric shook his head firmly.
“Absolutely not,” he said, placing his card down before I could even touch my wallet. “A man pays on the first date.”
His tone surprised me—not just polite, but final, like an unbreakable rule.
I hesitated for a second, then shrugged. “Okay, if you insist. Thank you.”
We walked out together, and he asked if he could call me soon.
“I’d like that,” I replied, meaning it.
He hugged me goodbye—just the right mix of friendly and interested. I drove home with a smile, thinking it had been one of the most amazing first dates I’d ever been on.
Then the next morning, I woke up to a notification from Eric. Still groggy, I expected a cute “Had a great time” text. Instead, I saw an attachment.
Curious, I opened it.
It was an invoice. A detailed, professional-looking invoice.
At the top, bold letters read:
Date Night Invoice – Amount Due: 1 Outstanding Balance.
I nearly choked on my coffee.
He had itemized “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
But the kicker?
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.
Not only was he demanding “payment”—he was charging me with mandatory affection?! Who does that?!
I screenshotted it 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 typed, still in disbelief. “He’s SERIOUS!”
Five minutes later, my phone rang. Chris was howling with laughter.
“Kelly, I can’t believe this,” he gasped. “I’ve known this dude for years and NEVER thought he’d pull something this insane.”
“So, this isn’t a joke?” I asked.
“Nope,” Chris confirmed. “He’s always been weird about dating, but THIS? Next level. Okay, we need to get back at him.”
Chris, the king of pettiness, hatched a plan. An hour later, he sent me an identical invoice—except this time, it charged Eric for my suffering.
- 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
“THIS IS PERFECT,” I texted. “SEND IT!”
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 sent a thumbs-up emoji and blocked him.
Later, Mia called, still laughing. “I really thought he was normal!”
“Hey, don’t feel bad,” I chuckled. “At least we got a great story out of it.”
And that was how I learned the golden rule of dating: If a guy insists on paying, make sure he’s not going to send you an invoice afterward.
The keychain, though? I kept it. Not as a memory of Eric—but as the funniest souvenir from the weirdest date of my life.
