When my brother set me up with a “perfect gentleman,” I was skeptical. Flowers, charm, and a smile made me wonder if he was the real deal. But when he insisted on driving me home, my gut whispered: Don’t. I should’ve listened.
You know when someone swears they’ve found “the perfect guy” for you? That’s how this disaster began.
My brother Marcus wouldn’t stop talking about Andy, a guy from his pickleball group. “Polite, smart, good job. Single too long,” Marcus said, refilling his protein shake.
I rolled my eyes. “That’s what you said about Kevin—the spoon collector.”
“Andy’s different,” Marcus insisted, his tone half teasing, half hopeful. Something in his voice made me pause mid-chop, massacring carrots like they were stand-ins for my dating frustrations.
Brothers never give up. I was tired of “nice guys” with hidden expiration dates, but Marcus’s hope wore me down. Maybe I was just tired of being the perpetually single sister at family dinners. “Fine,” I said. “One date.” Famous last words.
Saturday night, I adjusted my dress for the fifth time. Why do we torture ourselves for strangers who might collect belly button lint?
At seven sharp, the doorbell rang. Andy stood there with wildflowers wrapped in brown paper. Tall, adorable, freshly pressed shirt, earnest smile.
“I didn’t know your favorites,” he said, handing me the bouquet. “But these looked pretty.”
“They’re perfect,” I replied. He waited patiently while I found a vase—no phone-checking, no sighs. Already a good sign.
Dinner was better than expected. He opened doors, pulled out my chair, asked about my job like he cared.
“I admire people who do what they love,” he said when I mentioned graphic design. When I praised the food, he added, “Our waiter deserves the real five stars.”
I softened, terrified. Maybe this time was different. Spoiler: it wasn’t.
When the check came, I reached for my phone to call an Uber. My rule: no rides home on first dates. Safer, fewer awkward doorstep moments.
Andy looked surprised. “No way. A gentleman drives his date home and watches her walk inside safely.”
I should’ve stuck to my rule. But his sincerity—and that smile—made me cave. He opened the car door like it was 1954, drove me home without checking his phone, and waited until I was inside. I waved from the window; he waved back.
That night, I felt something rare: safe. Maybe even lucky.
The next morning, my phone buzzed. A PayPal request—from Andy.
Gas: $4.75 Car depreciation: $3.50 Parking: $20 Cleaning fee for “puddle splash marks”: $9 Total: $37.25
I stared, then laughed so hard I nearly dropped my coffee. He had itemized the cost of basic decency and sent me a bill.
I sent him $50 with a note: “Thirteen-dollar tip for opening my door. Cheers.” Then I blocked him.
Marcus called later, shocked. “Sarah, I’m so sorry. I had no idea.”
“How could you? I bet he saves his charm for dates.”
Marcus sighed. “Actually, he bragged at pickleball this morning. Said it was like a rom-com. But when I showed the guys your screenshot, Andy muttered: ‘Chivalry doesn’t pay for itself.’”
He tried to defend himself, claiming modern women should appreciate “transparency in dating expenses.” The group voted him out of pickleball. Unanimously.
Here’s the twist: a week later, I saw a TikTok. Another woman shared screenshots of an “itemized date invoice” from Andy. Gas, depreciation, parking, cleaning fees—the same ridiculous breakdown.
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: “Your pickleball friend is TikTok famous.” His reply: “I’m never trusting my judgment about men again.”
Oddly enough, I’m grateful. Andy gave me the best story I’ve had in years—and a lesson: sometimes the worst dates make the best warnings.
I’m still dating, still rolling my eyes at Marcus’s suggestions, still single. But now I always take my own ride home, smiling at the thought that any man worth keeping won’t send me a bill for his efforts.
