The Perfect Gentleman (Who Sent Me a Bill)
You know when your brother says, “I’ve got the perfect guy for you!” and you just know it’s going to be a disaster? Yeah. That’s exactly how this train wreck started.
Marcus, my ever-enthusiastic brother, had been raving about this guy Andy from his Saturday pickleball group for weeks.
“But he’s not like the others,” Marcus insisted, leaning against my kitchen counter, shaking his protein shaker like it held the secrets of the universe. “Polite. Smart. Good job. And somehow still single—which, honestly, is a mystery.”
I rolled my eyes so hard I saw my own brain. “That’s what you said about Kevin, remember? The guy who collected antique spoons and cried when I used one to eat yogurt?”
“Andy’s different,” Marcus said, and there was something in his voice—half teasing, half annoyingly sincere—that made me pause mid-chop. (I was aggressively dicing carrots for dinner, taking out my dating frustrations on innocent vegetables.)
Here’s the thing about brothers: they’re like stubborn salesmen. They never give up. I’d had my fill of “nice guys” who turned out to be walking red flags, but Marcus’s hopeful puppy-dog look wore me down.
“Fine,” I sighed. “One date. Just to prove I’m open to this disaster.”
Famous. Last. Words.
The Date That Seemed Too Good to Be True
Fast-forward to Saturday night. I stood in front of my mirror, adjusting my dress for the fifth time, wondering why I even bothered.
Why do we do this to ourselves? I thought. Dress up, do our hair, all for a guy who might turn out to have a secret collection of toenail clippings or something.
At exactly 7 PM, the doorbell rang.
I took a deep breath, opened the door—and there he was.
Andy.
Tall, unfairly handsome, wearing a crisp button-down like he’d stepped out of a rom-com. And in his hands? A small bouquet of wildflowers wrapped in brown paper.
“I didn’t know your favorites,” he said, smiling in a way that made my stomach do a weird little flip. “But I thought these looked pretty.”
“They’re perfect,” I said, genuinely touched.
And then—get this—he waited while I found a vase, filled it with water, and arranged the flowers. No impatient sighs, no checking his phone. Just… patient.
“Ready?” he asked, and then—oh my God—he opened the car door for me.
I know, I know. It sounds old-fashioned. But when’s the last time someone actually did that? I was half expecting him to pull out a top hat and monocle next.
Dinner was… weirdly good.
He held doors. Pulled out my chair. Asked about my job like he actually cared.
When I told him I was a graphic designer, he said, “I always admire people who do what they love. Not everyone has the guts.”
And when I complimented the food, he grinned and said, “Right? But our waiter deserves the real five stars.”
I found myself softening. Which, honestly, terrified me.
Because you know how it goes—you start thinking, Maybe this one’s different. Maybe he doesn’t have a secret wife or a weird obsession with taxidermy.
Spoiler alert: He did.
The Gut Feeling I Should’ve Listened To
When the check came, I instinctively reached for my phone to call an Uber.
“No way,” Andy said, shaking his head like I’d just suggested we rob the place. “A gentleman drives his date home and makes sure she gets inside safely.”
Now, I should have stuck to my rule. Never let a first date drive you home. But that damn smile of his made me forget every sensible boundary I’d ever set.
So I caved.
He opened the car door like we were in a 1950s movie, drove me home without checking his phone once, and waited until I was safely inside before driving off.
I went to bed that night feeling something I hadn’t in months—happy. Hopeful. Maybe even… lucky.
Big mistake.
The Invoice of Doom
The next morning, my phone buzzed at 7:13 AM.
A PayPal request.
At first, I thought it was spam. But when I opened it and saw Andy’s name, my brain short-circuited.
Gas (restaurant to your place): $4.75
Car depreciation: $3.50
Parking: $20
Cleaning fee (puddle splash marks): $9
Total: $37.25
I stared at my screen. Blinked. Stared some more.
Then I laughed so hard I nearly choked on my coffee.
This man—this “perfect gentleman”—had itemized the cost of basic human decency and sent me a bill for it.
I mean, what kind of thought process even is that? “You know what would really cap off this lovely evening? An invoice.”
I sent him $50 with a note: “Thirteen-dollar tip for opening my door. Cheers.”
Then I blocked his number.
But the best part? It got better.
The Fallout (And the TikTok That Exposed Him)
I immediately texted Marcus: “Truly a mystery why he’s still single.”
Attached: Screenshots of Andy’s invoice and my response.
Marcus called me an hour later, equal parts horrified and amused.
“Sarah, I had no idea he was like this.”
“How could you? I bet he saves his special charm for the ladies.”
“Actually,” Marcus said, lowering his voice like he was sharing classified intel, “he was at pickleball this morning bragging about your date. Said it was ‘like something out of a rom-com.’”
I snorted. “Oh, it was movie-worthy. Just not the genre he was thinking of.”
“Yeah, well, when I showed the guys your screenshot, the whole group went silent. Then Andy muttered something I’ll never forget: ‘Chivalry doesn’t pay for itself.’”
HE DID NOT.
“Oh, he did,” Marcus confirmed. “And then he tried to defend himself, saying modern women should appreciate ‘transparency in dating expenses.’”
I was wheezing with laughter. “Please tell me you’re joking.”
“Wish I was. Needless to say, he won’t be joining us for pickleball anymore.”
The guys had voted him out. Unanimously.
But wait—it gets better.
Last weekend, I was scrolling through TikTok when I choked on my coffee.
There, on my screen, was a girl sharing screenshots of an “itemized date invoice” from a guy named Andy.
The amounts were slightly different, but the audacity was identical. Gas. Car depreciation. Parking. Cleaning fees.
“This guy thinks he’s Uber with dinner service,” the girl said, shaking her head.
HE’D DONE THIS BEFORE.
This wasn’t a weird one-off. This was his dating strategy.
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 ever again.”
The Lesson (And the Silver Lining)
Here’s the weirdest part: I’m grateful for Andy.
He gave me the best story I’ve had in years. And more importantly, he taught me something:
Sometimes the worst dates make the best lessons.
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 that any man worth keeping around won’t send me a bill for his efforts.