When my brother insisted I go on a date with his friend Andy, I finally gave in. To my surprise, Andy was charming, polite, and thoughtful — even bringing flowers and opening doors. Dinner went smoothly, and when he offered to drive me home, I hesitated but agreed, breaking my usual “no rides on first dates” rule. The evening felt refreshingly genuine, and for the first time in a while, I let my guard down.
But the next morning, my phone buzzed with something unexpected: a PayPal request from Andy. He had itemized the costs of the night — gas, parking, car depreciation, even a “cleaning fee” for puddle splashes — totaling $37.25. At first, I thought it was a joke. It wasn’t. I laughed, sent him $50 with a sarcastic tip, and blocked his number. It was the fastest a first impression had ever unraveled.
When I told my brother and showed him the screenshots, he was stunned. Turns out, Andy bragged about the date to their pickleball group — until the receipt surfaced. The group voted to stop inviting him, and I thought that was the end of it. But days later, I found a TikTok from another woman sharing a nearly identical invoice — same guy, same tactics.
The experience went viral, and suddenly Andy’s behavior became internet infamous. Though the date didn’t turn out as hoped, I walked away with a story that still makes my friends laugh — and a reminder that red flags come in all forms. Now, I always trust my instincts and book my own ride home.