My brother had been on a mission to set me up for months. Every family dinner, every phone call somehow ended with, “I know the perfect guy for you.” I had heard it too many times to count. Usually, I brushed him off, but one evening, just to stop the endless suggestions, I gave in. “Fine,” I said, “one date. That’s it.”
When Andy showed up at my door, holding a bunch of wildflowers and wearing a smile that seemed both kind and confident, I was caught off guard. He had that old-fashioned politeness you rarely see anymore—he complimented me without being over the top, held the door open, and even thanked me for agreeing to meet him. For the first time in a long while, I thought maybe my brother had finally gotten something right.
Dinner was… nice. Simple, easy, comfortable. He asked genuine questions instead of talking only about himself. He listened when I answered, laughed at my dry jokes, and never once reached for his phone. I realized how rare it was to sit across from someone who seemed fully present. By dessert, I felt a lightness I hadn’t felt in years. Maybe this wasn’t a setup disaster after all.
When the evening wrapped up, I went to order my ride home. I’ve always had one rule about first dates: never let a man drive me home. It’s about safety, sure, but also about boundaries. Andy, however, insisted. “Come on,” he said with a polite smile. “A gentleman makes sure his date gets home safely.” I hesitated, then reluctantly agreed. The ride was quiet but pleasant, and he dropped me off right at my building with a friendly wave. No awkward lingering, no uncomfortable comments. Just a polite goodbye.
I went to bed smiling that night, thinking maybe I had met someone different—someone kind, respectful, and sincere. It felt like the end of a sweet movie scene. I even texted my brother, telling him he might’ve finally been right. But the next morning shattered that little daydream.
When I checked my phone, there it was—a PayPal request from Andy. At first, I thought it had to be a mistake. Then I opened it and saw a detailed breakdown: “Dinner cost share,” “Gas,” “Parking,” “Car wear-and-tear,” and, my personal favorite, a “cleaning fee.” I actually laughed out loud. Was this man serious?
Still laughing, I sent him more than he’d asked for, added a sarcastic “tip,” and blocked him immediately. A few hours later, my brother called. He was half-laughing, half-apologizing. Apparently, Andy had bragged to his friends about what a “perfect date” he’d been—until they saw the invoice. None of them were impressed. My brother ended the story with, “Yeah, he won’t be joining our pickleball group anymore.”
A week later, I stumbled upon a video online. A woman was sharing almost the exact same story—same kind of guy, same fake politeness, same ridiculous “invoice” afterward. It turned out Andy had a habit of doing this, almost like a personal policy. Instead of feeling angry, I actually found myself laughing again.
That strange experience, as frustrating as it could’ve been, ended up teaching me something valuable. Real kindness doesn’t come with a price tag. The right person won’t turn a date into a transaction or measure generosity by a receipt.
I’m still dating, still hopeful, and definitely more tuned in to my instincts. And if nothing else, I’ve learned one thing for sure: I’ll always trust my gut—and I’ll always, always order my own ride home.