The Worst First Date Ever: A Gentleman with a Price Tag
When my best friend Mia insisted on setting me up with her boyfriend’s friend, I was skeptical. But she swore he was perfect for me.
“Kelly, trust me—Eric is a total gentleman. You’ll love him!” Mia gushed over the phone as I dug through my closet, trying to find something cute to wear.
“You’ve never played matchmaker before,” I reminded her. “How do you even know what my type is?”
“Because I know you better than anyone!” she shot back. “Plus, Chris says Eric’s a great guy. They’ve been friends forever.”
That made me pause. Chris, Mia’s boyfriend, was a solid judge of character. If he vouched for Eric, maybe this wasn’t a complete disaster.
“Fine,” I sighed. “At least send me a picture.”
Seconds later, my phone buzzed. The guy in the photo was handsome—clean-cut, well-dressed, with a warm smile that actually reached his eyes.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him! You won’t regret it!”
After some light texting, we agreed to meet at a nice Italian restaurant by the river. Not too fancy, but classy enough for a first date.
The Date That Felt Too Good to Be True
I arrived five minutes early, nervously checking my reflection in my phone. Then I saw him walking toward me—tall, confident, and holding… a bouquet of roses?
Not just any roses. These were professional—tied with a silky ribbon, the kind you’d get from an actual florist.
“You must be Kelly,” he said, flashing that same charming smile from his picture. “These are for you.”
“Wow, thank you!” I said, genuinely stunned. “You didn’t have to do this.”
“I wanted to make a good first impression,” he replied smoothly.
But he wasn’t done.
From his jacket pocket, he pulled out a small gift box with a shiny cyan bow.
“What’s this?” I asked, my eyebrows shooting up.
“Open it,” he urged.
Inside was a sleek silver keychain with my initial—“K”—engraved on it.
“Mia mentioned you like personalized things,” he said with a grin.
At this point, I was impressed. Flowers and a thoughtful gift? Either this guy was really into me, or he was the king of first-date grand gestures.
The rest of the night only got better. He pulled out my chair, asked deep questions about my life, and actually listened to my answers. We bonded over true crime podcasts and weird documentaries.
He told hilarious stories about his marketing job, and by the time dessert came, I was thinking: This might be the best first date I’ve ever had.
Then the check arrived.
I reached for my purse, but Eric stopped me with a firm hand.
“Absolutely not,” he said, slapping down his credit card. “A man always pays on the first date.”
His tone wasn’t just polite—it was final, like he was reciting an unbreakable law.
I shrugged. “Okay, if you insist. Thank you.”
We said goodbye with a perfect hug—friendly but flirty—and I drove home grinning, thinking, Wow, Mia was right. He’s amazing.
The Morning After: The Invoice from Hell
The next day, I woke up to a notification from Eric. Still half-asleep, I expected a sweet “Had a great time!” text.
Instead, I saw an attachment.
I grabbed my coffee, settled back into bed, and opened it—maybe it was a cute photo from last night?
Nope.
It was an invoice.
A professional, itemized invoice titled:
DATE NIGHT INVOICE – AMOUNT DUE: 1 OUTSTANDING BALANCE
My stomach dropped as I read the breakdown:
- 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 at the bottom, in bold:
“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.
This wasn’t a joke. He actually expected me to pay him back in affection and dates for what he’d willingly spent on me.
I immediately screenshot it 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 texted back.
“WAIT TILL CHRIS SEES THIS. HE’S GOING TO LOSE IT.”
Five minutes later, my phone rang. It was Chris—howling with laughter.
“Kelly, I can’t believe this,” he gasped between laughs. *”I’ve known Eric for *years* and never, ever thought he’d pull something this insane.”*
“So this isn’t some weird joke?” I asked.
“Nope,” Chris confirmed. *”He’s always been intense about dating, but this is next-level crazy. Don’t worry—I’ve got the *perfect* payback.”*
The Ultimate Revenge Invoice
Chris, the king of petty revenge, crafted an identical invoice—but way better.
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 cackled as I read it. “Send it!”
Chris forwarded it to Eric.
Within minutes, my phone blew up with angry texts:
“Wow, really mature.”
“I was just setting expectations. Not everyone is rich.”
“Chris is a terrible friend.”
“You just missed out on a GREAT guy.”
I didn’t even bother responding. Instead, I sent a single 👍 emoji and blocked him.
Mia called me later, still laughing. *”I’m *so* sorry. I had no idea he was like this!”*
“Don’t worry,” I said, grinning. “At least we got a hilarious story out of it.”
*”Oh, this is *definitely* getting told at every party for the next ten years,”* she agreed.
The Lesson Learned
From now on, I have one golden dating rule:
If a guy insists on paying, make sure he’s not going to send you an invoice afterward.
As for the keychain?
I kept it. Not because it reminded me of Eric, but because it was the perfect souvenir from the weirdest date of my life.