My brother Marcus has always acted like he’s the family’s personal Cupid — even though none of his matches have ever worked out. The last guy he set me up with spent our entire date showing me photos of his vintage spoon collection as if they were his children. So when he started hyping up some pickleball buddy named Andy, I mentally prepared myself for another disaster.
But Marcus wouldn’t drop it. For weeks.
“Sarah, seriously,” he kept insisting. “Andy’s a catch — smart, respectful, financially stable, owns property, drives a nice car. And he’s picky. Really picky. If he’s interested in you, that’s a big deal.”
He was pitching the man like he was trying to sell him to a bank loan officer. I finally gave in — partly because Marcus wouldn’t stop, partly because being the only single sibling at family gatherings was getting old.
“One date,” I warned him. “Just one.”
Marcus lit up like he’d won a raffle. “You’ll thank me,” he declared.
Spoiler: I would not.
But it took a bit before the red flags showed up.
Andy arrived on Saturday with a bouquet of wildflowers wrapped in kraft paper — charming, understated, actually sweet. He looked polished and professional, opened the car door for me, asked thoughtful questions, listened, and didn’t touch his phone once. By the middle of our dinner at a small Italian place, I found myself thinking maybe — just maybe — Marcus had finally done something right.
He talked about his accounting job in a surprisingly interesting way, loved hiking, read real books, and treated the server politely. He even noticed an art print near my kitchen and complimented it. I genuinely started to relax for the first time in a long time.
Then came the moment I wish I’d trusted my own rules.
As we waited for the check, I pulled out my phone to call an Uber. Not because I didn’t trust him — just because I have a firm rule: no rides home on a first date. Clear boundary, clean exit.
But Andy looked perplexed.
“Why? I brought you here,” he said. “A gentleman drives his date home.”
Usually, I’d stick to my rules. But he sounded sincere, not pushy. And he didn’t linger at my door afterward — just wished me a good night and drove away.
I went to bed cautiously optimistic.
Then came the next morning.
At 7:13 a.m., I got a PayPal notification. I assumed it was spam… until I saw the name.
Andy had sent me a bill.
A literal, itemized invoice labeled “Reimbursement for transportation expenses.”
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Gas from restaurant to your home: $4.75
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Vehicle wear-and-tear: $3.50
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Downtown parking: $20.00
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Cleaning fee for water spots on passenger door: $9.00
Total: $37.25
Plus a note:
“Thanks for a great evening. Please pay when you can. — Andy”
I just stared.
Then I laughed so hard I nearly choked.
I took screenshots and immediately sent them to Marcus with one message:
“Your friend sent me a receipt.”
Then I made myself a coffee and crafted the perfect reply. If Andy thought dating was a business transaction, I’d treat it like one.
I sent him $50 — the amount he requested plus a generous tip — with this message:
“Thanks for the detailed invoice. Here’s $37.25 plus a gratuity for exemplary door-opening, chair-pulling, and comedic entertainment. Please leave a 5-star review. Also, I never want to see you again.”
Blocked.
Ten minutes later, Marcus called me, horrified. Andy had already bragged to his pickleball group about our date, declaring I was “wife material.” When his friends asked about the invoice, he said:
“Chivalry doesn’t pay for itself.”
They kicked him out of the pickleball group on the spot.
But it got better.
A week later, I saw a viral TikTok from a woman holding — you guessed it — an itemized bill from a guy named Andy. Same tone. Same categories. This one also charged:
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“Cologne and grooming prep: $15”
The comments were ruthless.
“This is Uber, but for psychos.”
“He charged her for oxygen exposure.”
“This man is sending invoices instead of red flags.”
Then more women came forward.
Screenshots. Venmo requests. “Emotional labor fees.” “Mileage charges.” One woman said he billed her for “romantic overhead.”
Turns out Andy was running a full accounting department out of his dating life — and a lot of us had mistaken his polished manners for genuine decency.
He wasn’t being charming. He was performing. Every nice gesture was something he planned to charge for later.
But his ridiculous behavior sparked a bigger conversation. Women started sharing stories about men who kept mental scorecards, expected repayment for basic courtesy, or treated dating like an investment they were owed returns on. Andy was just the extreme example.
Here’s what I learned:
A good man doesn’t invoice you for being polite.
A respectful man doesn’t turn kindness into debt.
And if someone insists on driving you home, then charges you for the gas… run.
I’ve kept my rule since then: I always take my own ride home.
Marcus has officially retired from matchmaking forever.
Now, it’s one of my favorite stories to tell — a reminder that red flags sometimes come wrapped in politeness, and that the strangest men teach the clearest lessons.
Andy’s flowers wilted after a week.
His invoice became legendary.
And here’s the truth:
If a man treats courtesy like a service…
he’s not a gentleman — he’s a walking receipt.
Block him, laugh about him, and move on.