My Date Insisted on Driving Me Home – I Wish I’d Said No #5

You know when someone says they have “the perfect guy” for you? Yeah, that’s exactly how this whole disaster started.

My brother Marcus had been going on about this Andy guy from his Saturday morning pickleball group for weeks.

“But he’s not just any guy,” Marcus said, smirking as he refilled his protein shake at my kitchen counter. “Polite. Smart. Good job. Still single, though, for too long, if you ask me.”

I rolled my eyes so hard I’m surprised they didn’t fall out of my head.

“That’s what you said about Kevin, remember? The vintage spoon collector?”

“Andy’s different,” Marcus insisted, and there was something in his voice, half teasing, half genuinely hopeful, that made me pause mid-chop.

I was massacring some poor carrots for dinner, taking out my dating frustrations on root vegetables like any reasonable person would.

Here’s the thing about brothers: they never give up. I’d honestly had enough of “nice guys” with hidden expiration dates, but something about Marcus’s tone wore me down.

Maybe it was the way he looked so hopeful, or maybe I was just tired of being the perpetually single woman at family dinners.

“Fine,” I said finally. “One date. Just to prove I’m open to this whole thing.”

Famous last words, right?

So there I was the following Saturday, standing in front of my bedroom mirror, adjusting my dress for the fifth time.

Why do we do this to ourselves? I mean, what’s the point of trying to look perfect for someone who might turn out to collect belly button lint or something equally disturbing?

At exactly seven o’clock, my doorbell rang.

I took a deep breath, grabbed my purse, and opened the door to find Andy holding a small bouquet of wildflowers wrapped in brown paper.

He was tall, adorable, and wearing a button-down that looked freshly pressed. His smile was so earnest it almost made me forget about Kevin and his spoon obsession.

“I didn’t know your favorites,” he said, extending the flowers toward me, “but I thought these looked pretty.”

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

And you know what? 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 his foot, no subtle sighs of frustration.

“Ready?” he asked, and then — get this — he opened the car door for me.

I know, I know, it sounds old-fashioned, but when’s the last time someone did that for you? I was genuinely surprised.

Dinner was even better than I’d expected. He held doors, pulled out my chair, and asked about my job like he cared about the answer.

When I told him about my work 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 said, “Right? But I think our waiter deserves the real five stars.”

I found myself softening, which frankly terrified me.

You know how it is: you start to think maybe this time will be different. Maybe this guy won’t have some weird deal-breaker hiding in his back pocket.

Spoiler alert: those guys always have a deal-breaker.

When the check came, I instinctively reached for my phone to call an Uber. I have a rule, see, no rides home on first dates. It’s just safer that way and avoids any misunderstandings at the front door.

Andy looked genuinely surprised.

“No way,” he said, laughing gently. “A gentleman drives his date home and watches her walk inside safely.”

Now, I should have stuck to my rule. I really should have, but he looked so sincere, and that smile was back, the one that made me forget about all my carefully constructed dating boundaries.

So I caved. Sue me.

He opened the car door like we were living in 1954, drove me all the way home without checking his phone once, and stayed parked until I got to my door.

When I turned to wave from my living room window, he waved back before driving away.

I went to bed that night feeling something I hadn’t felt in months: safe. Maybe even lucky. Can you believe that? I thought I might have found one of the good ones.

The next morning, my phone buzzed at 7:13 a.m. with a notification that made me blink hard, convinced I was still dreaming.

A PayPal request. At first, I thought it was spam (you know how those scammers work), but when I opened it and saw Andy’s name, my brain just… stopped working for a moment.

Are you ready for this? Because I’m not sure I was.

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 what I was seeing.

Then I laughed so hard I nearly dropped my coffee mug.

This man, who had seemed so perfect just 12 hours earlier, had actually itemized the cost of basic human decency and sent me a bill for it. Can you even imagine?

I mean, what goes through someone’s mind when they think, “You know what would cap 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 a second thought.

But I wasn’t done. Oh no, I was just getting started.

I immediately texted my brother: “Truly a mystery why he’s still single,” followed by screenshots of both Andy’s invoice and my response.

I spent the rest of the morning on my couch, periodically bursting into fresh waves of laughter. Every time I looked at my phone, I’d start giggling again. It was like my brain couldn’t quite accept that this had truly happened.

Around noon, Marcus called, and 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’m betting he saves his special charm for the ladies.”

“Actually,” Marcus said, his voice taking on that storyteller tone he gets when he has really good gossip, “there’s more. He was at pickleball this morning, bragging to all 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.”

“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. And then he tried to defend himself, saying modern women should appreciate transparency in dating expenses.”

I was laughing again, the kind of laugh that makes your sides hurt. “Please tell me you’re joking.”

“I wish I was. Needless to say, he won’t be joining us for Saturday morning pickleball anymore.”

The guys had voted him out. Unanimously. I have to admit, that felt pretty good.

But here’s where the story gets really interesting.

Last weekend, I was doing my usual Saturday morning routine: sprawled on my couch, coffee in hand, scrolling through TikTok with the dedication of someone who had nowhere else to be.

Suddenly, I choked on my coffee and nearly dropped my phone.

There, on my screen, was a video of a girl sharing screenshots of what she called an “itemized date invoice” from a guy called Andy.

The amounts were slightly different, but the audacious entitlement was exactly the same. Gas, car depreciation, parking, cleaning fees; the whole ridiculous breakdown.

“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 some weird one-off moment of poor judgment, oh no, this was his actual dating strategy. Can you imagine?

The comments section was absolutely brutal, 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 simple message: “Your pickleball friend is TikTok famous.”

His response was immediate: “I’m never trusting my judgment about men ever again.”

I spent the rest of the afternoon reading comments and sharing the video with friends. It turned into this whole group chat about dating horror stories, and honestly? It was therapeutic. At least my guy waited until after the date to reveal his true colors.

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 my brother’s suggestions, still single.

But now I always take my own ride home, and I do it with a smile, knowing that any man worth keeping around won’t send me a bill for his efforts.

Here’s another story: Every Sunday, I shopped at my SIL’s boutique to help her stay afloat. Candles, pillows, decor — I spent hundreds out of love. But one morning, I arrived early with coffee and overheard a conversation that left me speechless. One betrayal deserves another, so I set out to expose her.