You ever hear someone say, “I’ve got the perfect guy for you”? Yeah, that’s exactly how my whole disaster began.
My brother Marcus wouldn’t stop talking about this guy Andy, from his Saturday morning pickleball group.
“But he’s not just any guy,” Marcus said, smirking while he refilled his protein shake at my kitchen counter. “Polite. Smart. Good job. Still single though, for way too long, if you ask me.”
I rolled my eyes so hard I swear they almost fell out.
“That’s what you said about Kevin, remember? The guy who collected vintage spoons?”
Marcus waved me off, “Andy’s different.” There was something in his voice — part teasing, part serious — that made me pause mid-chop as I was chopping carrots for dinner. I was taking out all my dating frustrations on those poor vegetables, just like anyone would.
Here’s the thing about brothers: they never give up. I was honestly tired of “nice guys” who always ended up having some hidden problem. But something about Marcus’s tone wore me down.
Maybe it was how hopeful he looked. Or maybe I was just sick of being the forever-single woman at family dinners.
“Fine,” I said, sighing. “One date. Just to prove I’m trying.”
Famous last words, right?
So there I was the next Saturday night, standing in front of my bedroom mirror, fixing my dress for the fifth time.
Why do we do this to ourselves? Trying to look perfect for someone who might turn out to be a total weirdo? Like, who cares if he collects belly button lint or something?
At exactly seven o’clock, my doorbell rang.
I took a deep breath, grabbed my purse, and opened the door.
Andy was standing there holding a small bouquet of wildflowers wrapped in brown paper.
He was tall, cute, wearing a freshly pressed button-down shirt. His smile was so honest and sweet it almost made me forget about Kevin and his creepy spoon collection.
“I didn’t know your favorites,” Andy said, handing me the flowers. “But I thought these looked pretty.”
“They’re perfect,” I smiled, feeling a little flutter in my chest. “Thank you.”
He waited patiently while I grabbed a glass, filled it with water, and carefully placed the flowers on my dining table. No checking his phone, no tapping his foot, no sighing in boredom.
“Ready?” he asked, then — and this really surprised me — he opened the car door for me.
I know, it sounds old-fashioned, but seriously, when was the last time someone did that for you? I was genuinely impressed.
Dinner was even better than I’d hoped. He held the doors, pulled out my chair, and asked about my job like he actually cared.
When I told him I worked in graphic design, he said, “I always admire people who do what they love. Not everyone has the guts.”
And when I complimented the food, he added with a grin, “Right? But I think our waiter deserves the real five stars.”
I found myself relaxing around him, which honestly scared me a bit.
You know how it goes: you start to think maybe this time will be different. Maybe this guy won’t have a weird secret deal-breaker.
Spoiler alert: 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 stops any awkwardness at the front door.
Andy looked genuinely surprised.
“No way,” he laughed gently. “A gentleman drives his date home and watches her get inside safe.”
I should’ve stuck to my rule. Really, I should’ve.
But that smile — that sincere, warm smile — made me forget every carefully thought-out boundary I had.
So I gave in. Sue me.
He opened my car door like we’d stepped into a black-and-white movie from 1954, drove me all the way home without once checking his phone, and waited patiently until I was safely inside my apartment.
I waved to him from my living room window. He waved back before driving off.
I went to bed feeling something I hadn’t felt in months: safe. Maybe even lucky. Can you believe that? I thought I might have finally found one of the good ones.
Then the next morning, my phone buzzed at 7:13 a.m.
I blinked hard. It was a PayPal request.
At first, I thought it was spam — you know how scammers send those weird messages.
But it said Andy’s name.
And then I saw it.
He 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 thirty seconds, trying to understand what I was seeing.
Then I laughed so hard I almost dropped my coffee mug.
This man, who looked so perfect just 12 hours earlier, had actually made a detailed invoice for basic human kindness — and sent it to me.
Can you even imagine? What kind of mind thinks, “You know what would be great? An invoice.”
I sent him $50 with a note: “Thirteen-dollar tip for opening my door. Cheers.”
Then I blocked his number without a second thought.
But I wasn’t done.
I texted my brother immediately: “Truly a mystery why he’s still single,” and sent screenshots of the invoice and my reply.
I spent the rest of the morning on my couch, laughing over and over. Every time I looked at my phone, I’d start giggling again like it was a joke.
Around noon, Marcus called. I could hear both 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 special charm for other ladies.”
Marcus laughed, “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 definitely movie-worthy — just not the genre he was thinking of.”
Marcus said, “Yeah, well when I showed the guys your screenshot, the whole group 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 laughed until my sides hurt. “Please tell me you’re joking.”
“I wish I was. Needless to say, he’s not welcome at pickleball anymore.”
The guys voted him out. Unanimously.
Honestly, that felt pretty good.
But here’s where it gets even better.
Last weekend, I was doing my usual Saturday morning thing: lying on the couch, coffee in hand, scrolling through TikTok like I had nothing better to do.
Suddenly, I choked on my coffee and almost dropped my phone.
On my screen was a video of a girl sharing screenshots of an “itemized date invoice” from a guy named Andy.
The numbers were slightly different, but the crazy 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 said in the video.
I couldn’t believe it. Andy had done this before. This wasn’t a one-time bad idea — it was his actual dating strategy. Can you imagine?
The comment section was brutal, and I loved 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 simple message: “Your pickleball friend is TikTok famous now.”
His response was instant: “I’m never trusting my judgment about men again.”
I spent the rest of the afternoon sharing the video with friends. It turned into a group chat full of dating horror stories, and honestly? It felt good to laugh about it.
You know what the weirdest part is?
I’m actually grateful for Andy.
He gave me the best story I’ve had in years, and more importantly, he taught me something valuable: sometimes the worst dates make the best lessons.
I’m still dating, still rolling my eyes at Marcus’s suggestions, and yes — still single.
But now I always take my own ride home, and I do it with a smile.
Because any man worth keeping around? He won’t send you a bill for being decent.