The Worst First Date Ever: When a “Gentleman” Sent Me an Invoice
When my best friend Mia set me up on a blind date, I never expected things to go this wrong.
“He’s perfect for you, Kelly! Total gentleman—flowers, good job, the whole package,” Mia gushed over the phone as I dug through my closet, trying to find something cute to wear.
I hesitated. “You’ve never played matchmaker before. How do you even know he’s my type?”
Mia laughed. “Because I know you! Plus, Chris swears by him. They’ve been friends forever.”
That got my attention. Mia’s boyfriend, Chris, was a solid guy. If he vouched for Eric, maybe this wouldn’t be a disaster.
“Fine,” I sighed. “But send me a picture first.”
Seconds later, my phone buzzed with a photo. Eric was handsome—clean-cut, sharp smile, dressed like he stepped out of a business casual catalog.
“Okay, he’s cute,” I admitted.
“Told you!” Mia squealed. “Text him! You’re gonna love him.”
After some light texting, we set up dinner at a nice Italian spot by the river. Not too fancy, but classy enough for a first date.
The Too-Perfect First Impression
I arrived early, fidgeting by the entrance, checking my reflection in my phone. Then I saw him—tall, confident, and holding a bouquet of roses. Not the cheap gas station kind, but a real, ribbon-wrapped arrangement.
“You must be Kelly,” he said with a smooth smile. “These are for you.”
I blinked. “Wow, thank you! You didn’t have to—”
But he wasn’t done.
From his jacket pocket, he pulled out a small gift box with a shiny cyan bow.
My eyebrows shot up. “What’s this?”
“Open it,” he urged.
Inside was a sleek silver keychain with my initial, “K,” engraved on it.
Who does this on a first date?
“Something just for you,” he said. “Mia helped me pick it.”
Either this guy was really into me or he was the king of over-the-top first impressions.
The Charming (But Slightly Weird) Date
Eric was the full package—opened doors, pulled out my chair, asked deep questions. He remembered tiny details from our texts, like my job as a graphic designer and my sister’s name.
“So why’d you agree to this setup?” he asked between bites of pasta.
“Mia can be very convincing,” I laughed. “Plus, Chris vouched for you.”
“Chris is a great guy,” Eric nodded. “We go way back to college.”
The conversation flowed—true crime podcasts, weird documentaries, funny work stories. By the time the check came, I was thinking, This might be the best first date ever.
I reached for my wallet.
Eric slapped his card down fast. “Absolutely not. A man pays on the first date.”
His tone wasn’t just firm—it was final, like he was reciting a sacred rule.
I shrugged. “Okay, thanks.”
We said goodbye with a perfect hug—friendly but flirty. I drove home grinning, already planning our next date in my head.
The Morning After… Disaster
The next day, my phone buzzed with a message from Eric. I expected something sweet like, Had a great time!
Nope.
It was an invoice.
A real, professional-looking invoice titled:
DATE NIGHT INVOICE – AMOUNT DUE: 1 OUTSTANDING BALANCE
My stomach dropped.
At first, I thought it was a joke. But as I read, my coffee nearly came back up.
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 next date
Engaging Conversation: 1 compliment about my looks
Full Dinner + Tip Covered: A second date, no excuses
And the worst part?
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).
WHAT.
I immediately screenshot it and sent it to Mia.
Her reply was instant:
“OH. MY. GOD. I’M SHOWING CHRIS RIGHT NOW.”
Five minutes later, Chris called me—howling with laughter.
“Kelly, I swear, I had no idea he was like this!” he gasped between laughs. “This is next-level insane.”
“So… he’s serious?” I asked, still in shock.
“Dead serious,” Chris confirmed. “But don’t worry—I’ve got the perfect payback.”
The Ultimate Revenge Invoice
Chris, the master of petty revenge, drafted his own invoice and sent it to Eric.
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
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.
I cackled.
Eric’s response? A furious text storm:
“Wow, really mature.” “I was setting expectations!” “Chris is a terrible friend.” “You just lost out on a GREAT guy.”
I sent back a single 👍 and blocked him.
The Aftermath
Mia called me later, still laughing. “I’m so sorry. I really thought he was normal!”
“Don’t worry,” I said, grinning. “This is the best bad date story ever.”
And the keychain? I kept it—not because of Eric, but because it’s the ultimate souvenir from the weirdest date of my life.
Moral of the story? If a guy insists on paying, make sure he’s not going to bill you for it later.
