The Date Who Sent Me a Bill
You know when your brother says he’s found “the perfect guy” for you? Yeah, that’s how my nightmare began.
Marcus, my ever-enthusiastic big brother, had been raving about this guy Andy from his weekend pickleball group for weeks.
“He’s not like the others,” Marcus insisted, leaning against my kitchen counter, grinning like he’d just discovered the next big thing. “Polite. Smart. Great job. And—get this—still single. No idea why.”
I rolled my eyes so hard I nearly gave myself a headache.
“That’s exactly what you said about Kevin, the guy who collected antique spoons and cried when I used one to stir my coffee.”
“Andy’s different,” Marcus shot back, his voice dripping with confidence.
I was chopping carrots for dinner, taking out my dating frustrations on innocent vegetables. But something in his tone—half teasing, half annoyingly hopeful—made me pause.
Brothers. They never give up.
After weeks of pestering, I finally caved. “Fine. One date. But if he turns out to be another weirdo, you owe me a month’s worth of takeout.”
Famous last words.
The Perfect Gentleman… Or So It Seemed
Saturday night arrived, and I stood in front of my mirror, adjusting my dress for the hundredth time. Why do we do this to ourselves? I thought. What’s the point of dressing up for a guy who might secretly collect toenail clippings or something?
At exactly 7 PM, my doorbell rang.
I took a deep breath, opened the door—and there he was.
Andy.
Tall, charming, dressed in a crisp button-down, holding a small bouquet of wildflowers wrapped in brown paper.
“I didn’t know your favorites,” he said, handing them to me with a smile so warm it could melt butter. “But these looked like they’d suit you.”
“They’re beautiful,” I said, genuinely surprised.
And then—get this—he waited while I put them in water. No impatient sighs, no checking his phone. Just… patience.
When we got to his car, he opened the door for me. I know, right? When was the last time a guy did that?
Dinner was… shockingly nice. He listened, asked real questions, and even complimented the waiter.
“I always admire people who do what they love,” he said when I told him about my graphic design work. “Not everyone has the guts.”
I felt myself softening. Dangerous.
Because here’s the thing about dating: the moment you let your guard down, life loves to remind you why you had it up in the first place.
The Gut Feeling I Ignored
When the check came, I reached for my phone to call an Uber. First date rule: Never let them drive you home.
Andy looked almost offended.
“No way,” he said, shaking his head with a laugh. “A gentleman drives his date home and makes sure she gets inside safely.”
I should’ve said no. I knew I should’ve said no.
But he was so sincere. That smile, the manners, the way he made me feel like I was the only person in the room.
So I caved.
Big mistake.
He drove me home, waited until I was safely inside, and even waved from the car before driving off.
I went to bed thinking, Maybe… just maybe… I found one of the good ones.
The Morning After: The Invoice of Shame
At 7:13 AM, my phone buzzed.
A PayPal request.
From Andy.
I blinked, sure I was still dreaming.
But no. There it was.
Gas (restaurant to your place): $4.75
Car depreciation: $3.50
Parking: $20
Cleaning fee (puddle splash marks): $9
TOTAL: $37.25
I stared.
Then I laughed. Hard. So hard I nearly spilled my coffee.
This man—this “gentleman”—had itemized the cost of basic decency and sent me a bill for it.
Unbelievable.
I sent him $50 with a note: “Thirteen-dollar tip for opening my door. Cheers.”
Then I blocked his number.
But the fun wasn’t over.
The Fallout: Pickleball Justice
I immediately texted Marcus: “Truly a mystery why he’s still single.”
Attached: Screenshots of Andy’s invoice and my response.
Ten minutes later, my phone blew up.
Marcus called, half horrified, half laughing. “Sarah, I swear, I had no idea.”
“Clearly,” I said, still giggling.
“Well, get this,” Marcus said, lowering his voice like he was sharing top-secret gossip. “Andy showed up to pickleball this morning bragging about your date. Said it was ‘like something out of a rom-com.’”
I snorted. “Oh, it was cinematic, alright.”
“Yeah, well, when I showed the guys your screenshot, the whole group went silent. Then Andy muttered, ‘Chivalry doesn’t pay for itself.’”
“HE DID NOT.”
“Oh, he did. Then he tried to argue that ‘modern women should appreciate transparency in dating expenses.’”
I lost it. “Please tell me you kicked him out of the group.”
“Unanimous vote. He’s done.”
Justice. Sweet, sweet justice.
The Plot Twist: He’s Done This Before
A week later, I was scrolling through TikTok when I nearly choked on my coffee.
A girl was on my screen, holding up her phone with a screenshot of an itemized date invoice.
From Andy.
Gas. Car depreciation. Parking. Cleaning fees.
The exact same ridiculous breakdown.
“This guy thinks he’s Uber with dinner service,” she said, rolling her eyes.
The comments were brutal:
“Ladies, beware of Andy’s Taxi & Misogyny Service.”
“At least Uber gives you mints.”
“This man really said, ‘Pay me back for being a gentleman.’”
I sent the video to Marcus with one message: “Your pickleball friend is TikTok famous.”
His reply: “I’m never trusting my judgment about men again.”
The Lesson: Worst Dates Make the Best Stories
In the end, I’m weirdly grateful for Andy.
He gave me the best dating horror story I’ve ever had. And more importantly, he taught me two things:
- Always trust your gut. If it says “don’t get in the car,” listen.
- A real gentleman doesn’t send an invoice.
I’m still dating. Still rolling my eyes at Marcus’s suggestions. Still single.
But now?
I always take my own ride home. And I do it with a smile, knowing any man worth keeping would never charge me for basic human decency.
The end. (Or at least, the end of Andy’s dating career.)