You ever hear someone say, “I’ve got the perfect guy for you”? Yeah, well, that’s exactly how this disaster began.
My brother Marcus wouldn’t stop talking about this guy Andy from his Saturday morning pickleball group. Every time I saw him, he was like a broken record.
“But he’s not just any guy,” Marcus said, smirking as he refilled his protein shake right at my kitchen counter. “He’s polite. Smart. Has a good job. Still single, though, which makes no sense.”
I rolled my eyes so hard I swear they almost fell out.
“That’s what you said about Kevin last year. You know, the vintage spoon collector?” I teased.
Marcus gave me a look like, “He’s different, I swear.” There was this mix of teasing and real hope in his voice that made me pause mid-chop as I was hacking away at some poor carrots. Honestly, I was just taking out my dating frustrations on vegetables like any sane person would.
Here’s the truth about brothers: they never give up. I’d been done with “nice guys” who came with hidden expiration dates, but Marcus’s hopeful tone wore me down. Maybe it was because I was tired of being the single woman at every family dinner, or maybe it was the way he looked at me like he actually believed this time would be different.
“Fine,” I said, throwing down my knife. “One date. Just one. To prove I’m open to this whole thing.”
Famous last words.
So, the next Saturday evening, I stood in front of my bedroom mirror adjusting my dress for the fifth time. Why do we do this? Why try so hard to look perfect for someone who might end up being a belly-button lint collector or worse?
Right at seven, my doorbell rang. I took a deep breath, grabbed my purse, and opened the door.
There he was — Andy. Tall, adorable, in a freshly pressed button-down shirt, holding a small bouquet of wildflowers wrapped in brown paper.
“I didn’t know your favorites,” he said, holding out the flowers. “But I thought these looked pretty.”
“They’re perfect,” I smiled, feeling my guard drop just a little.
You know what made him stand out? He waited patiently while I found a glass, filled it with water, and arranged the flowers on my dining table. No checking his phone, no tapping feet, no sighing. Just calm, respectful patience.
“Ready?” he asked, and then—he actually opened the car door for me.
I know, I know, sounds old-fashioned. But when’s the last time anyone did that for you? I was genuinely surprised and, honestly, a little touched.
Dinner was better than I expected. Andy held doors, pulled out my chair, and asked about my job like he really cared.
When I told him I’m 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 laughed and said, “Right? But I think the waiter deserves the real five stars.”
I felt myself soften, and that scared me. You know how it is when you start to hope maybe this time, maybe this guy won’t have some awful secret lurking?
Spoiler: They always do.
When the check came, I reached for my phone to call an Uber. I have a rule: no rides home on first dates. It’s safer and keeps things clear.
Andy looked genuinely shocked. “No way,” he laughed gently. “A gentleman drives his date home and waits until she’s safely inside.”
I should have stuck to my rule. I really should have.
But that smile—the one that made me forget all my careful rules—won.
So I caved.
He opened the car door again, drove me all the way home without once checking his phone, and even stayed parked until I got to my door.
I waved from my window, and he waved back before driving off.
That night, I went to bed feeling something I hadn’t felt in months: safe. Maybe even lucky. Could you believe it? I thought, maybe, just maybe, I’d found one of the good ones.
Then the next morning, at exactly 7:13 a.m., my phone buzzed with a notification.
A PayPal request.
I blinked hard, convinced I was dreaming.
At first, I thought spam. But when I saw it was from Andy, my brain just froze.
He’d 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 my phone for a full 30 seconds, trying to process this insanity.
Then I laughed so hard I almost dropped my coffee mug.
This guy, who seemed perfect just 12 hours before, had actually itemized basic human decency and sent me an invoice.
Can you even imagine?
What goes through someone’s mind thinking, “You know what would top 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—without hesitation.
But I wasn’t done.
No, I was just getting started.
I immediately texted my brother: “Truly a mystery why he’s still single,” and sent him screenshots of the bill and my response.
I spent the rest of the morning on my couch, bursting into fresh waves of laughter every time I looked at my phone. It was like my brain couldn’t accept this really happened.
Around noon, Marcus called. I could hear the shock and amusement in his voice.
“Sarah, I’m so sorry. I had no idea he was like this.”
“How could you? I bet he saves his charm for the ladies.”
Marcus chuckled, then said, “Actually, there’s more. He was at pickleball this morning, bragging to the guys about your date. Said it was ‘like something out of a rom-com.’”
I snorted. “Oh, it was movie-worthy alright. Just not the kind he thought.”
Marcus laughed too. “Yeah, well, when I showed the guys your screenshot, the room went dead silent. Then Andy muttered something I’ll never forget: ‘Chivalry doesn’t pay for itself.’”
“He did not.”
“He absolutely did. Then he tried to defend himself, saying modern women should appreciate transparency in dating expenses.”
I was laughing so hard I nearly cried. “Please tell me you’re joking.”
“I wish I was. Needless to say, he won’t be joining us for pickleball anymore.”
The guys had voted him out. Unanimously. Honestly, that felt pretty great.
But wait, the story doesn’t end there.
Last weekend, I was doing my usual Saturday morning routine—lounging on the couch, coffee in hand, scrolling TikTok like a pro—when I choked on my coffee.
There, on my screen, was a video of a girl sharing screenshots of what she called an “itemized date invoice” from a guy named Andy.
The prices were slightly different, but the outrageous sense of entitlement was exactly the same: gas, car depreciation, parking, cleaning fees—the whole ridiculous list.
“This guy thinks he’s Uber with dinner service,” she joked in the video.
I couldn’t believe it. Andy had done this before. This wasn’t a one-time weird moment—it was his whole dating strategy.
The comments were savage, and I lived for every single one:
“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 a message: “Your pickleball friend is TikTok famous.”
His reply was instant: “I’m never trusting my judgment about men ever again.”
I spent the afternoon laughing and sharing the video with friends. It turned into a group chat filled with dating horror stories, and honestly? It was therapeutic.
At least my guy waited until after the date to reveal his true colors.
The weirdest part?
I’m actually grateful for Andy.
He gave me the best story I’ve had in years—and a great lesson: sometimes the worst dates make the best stories.
I’m still dating, still rolling my eyes at my brother’s suggestions, and still single.
But now, I always take my own ride home.
And I do it with a smile, knowing any man worth keeping around won’t send me a bill for just being decent.
