I Let My Date Drive Me Home — and Learned an Unexpected Lesson #5

My brother swore he had “the perfect guy” for me, and although I rolled my eyes, I agreed to one date just to stop the endless suggestions. When Andy showed up at my door with wildflowers, a warm smile, and genuine manners, I wondered if maybe — just maybe — this time could be different. Dinner went surprisingly well. He asked thoughtful questions, opened doors, and didn’t touch his phone once. For the first time in a long while, I felt safe, even a little hopeful.

When the evening ended, I went to call a ride home, sticking to my rule about not letting first dates drive me. But Andy insisted, saying a gentleman should make sure his date gets home safely. Against my instincts, I agreed, and he dropped me off without a single uncomfortable moment. I went to bed smiling, thinking I had met someone kind, respectful, and sincere. It felt like the ending to a sweet movie — or so I thought.

The next morning, reality hit like a bucket of ice water. A PayPal request popped up from Andy — a detailed “invoice” for the date, including gas, parking, car wear-and-tear, and even a “cleaning fee.” I laughed in disbelief before sending him more than he asked for with a sarcastic “tip,” then blocked him. Later that day my brother called, apologizing and telling me Andy had actually bragged about the date — until the other guys saw the invoice and weren’t impressed. Let’s just say he won’t be playing pickleball with them anymore.

A week later, someone posted a video online showing the same thing happening to her — turns out sending invoices after dates was his pattern. Instead of feeling frustrated, I found myself laughing again. That bizarre date taught me something important: kindness doesn’t come with a price tag, and genuine people don’t keep score. I’m still dating, still hopeful, and now I trust my instincts a little more — and always order my own ride home.