You know that moment when your brother swears he’s found “the perfect guy” for you? That’s exactly how this dating disaster began.

My brother Marcus had been hyping up Andy from his Saturday pickleball group for weeks.

“He’s not like the others,” Marcus said, smirking while refilling his protein shake in my kitchen. “Polite, smart, good job, and still single—for some reason.”

I rolled my eyes so hard it hurt. “That’s what you said about Kevin, the vintage spoon collector.”

“Andy’s different,” Marcus insisted, his voice half-teasing, half-hopeful. Something in his tone finally wore me down.

I was tired of being the single sister at every family dinner, so I gave in. “Fine. One date.”

Famous last words.

The following Saturday, I stood in front of my mirror adjusting my dress for the fifth time. At exactly 7 p.m., the doorbell rang. There was Andy, tall and genuinely cute, holding a small bouquet of wildflowers wrapped in brown paper.

“I didn’t know your favorites,” he said with an earnest smile, “but these looked pretty.”

“They’re perfect. Thank you.” I smiled back.

He waited patiently while I put the flowers in water—no phone-checking, no impatient sighs. Then he opened the car door for me like a true gentleman.

Dinner was surprisingly great. He held doors, pulled out my chair, and actually listened when I talked about my graphic design job. “I admire people who do what they love,” he said. “Not everyone has the guts.”

I started to relax. For once, maybe this guy was the real deal.

When the check arrived, I reached for my phone to order an Uber. I have a strict rule: no rides home on first dates. It keeps things safe and avoids awkward front-door moments.

But Andy laughed gently. “No way. A gentleman drives his date home and makes sure she gets inside safely.”

He looked so sincere, and that charming smile was back. Against my better judgment, I caved.

He opened the car door again, drove me straight home without touching his phone once, and waited until I was safely inside. From my living room window, I waved. He waved back and drove off.

I went to bed feeling something rare—safe and maybe even a little lucky. I thought I might have finally met one of the good ones.

The next morning at 7:13 a.m., my phone buzzed with a PayPal notification. At first I thought it was spam. Then I saw Andy’s name.

He had sent me a bill.

Gas from restaurant to my place: $4.75 Car depreciation: $3.50 Parking: $20 Cleaning fee for “puddle splash marks”: $9 Total: $37.25

I stared at the screen, frozen. Then I burst out laughing so hard I nearly spilled my coffee.

This man—who had played the perfect gentleman just hours earlier—had itemized the cost of basic decency and actually sent me an invoice.

I sent him $50 with a note: “$13 tip for opening my door. Cheers.” Then I blocked his number.

But I wasn’t done. I immediately texted my brother the screenshots: “Truly a mystery why he’s still single.”

Marcus called me around noon, his voice full of shock and amusement. “Sarah, I’m so sorry. I had no idea.”

He told me the rest: Andy had shown up at pickleball that morning bragging about our “rom-com” date. When Marcus showed the group the invoice screenshots, everyone went silent. Then Andy muttered, “Chivalry doesn’t pay for itself.”

The guys voted him out of the group on the spot.

I spent the rest of the morning on my couch, laughing until my sides hurt every time I thought about it.

Then last weekend, while scrolling TikTok, I choked on my coffee.

There it was—a video from another girl sharing screenshots of an almost identical “itemized date invoice” from a guy named Andy. Gas, depreciation, parking, cleaning fee—the whole ridiculous list. Slightly different amounts, but the same entitled vibe.

“This guy thinks he’s Uber with dinner service,” she said in the video.

The comments were savage: “Ladies, beware of Andy’s Taxi & Misogyny Service.” “At least he’s transparent… about being cheap.”

It turned out this wasn’t a one-off weird moment. It was Andy’s actual dating strategy.

I laughed even harder. Lesson learned: always trust your gut, never break your no-ride-home rule on a first date, and never let your brother set you up again without a full background check.

Now every time someone says they know “the perfect guy,” I just smile and remember Andy’s invoice. At least I got a great story—and $12.75 profit—out of it.