I Let My Date Drive Me Home — And I Still Regret It

My brother has always considered himself the family’s unofficial matchmaker, even though his success rate is embarrassingly low. After enduring one disastrous setup after another, I had learned to keep my expectations low. Still, he insisted for weeks that I meet a man he played sports with—a polite, well-spoken guy he claimed would be perfect for me. I agreed to go on just one date, mostly to stop the constant convincing.

To my surprise, the man seemed charming at first. He brought flowers, asked thoughtful questions, and treated the restaurant staff with respect. For the first part of the evening, I wondered if my brother had finally gotten something right. The date went smoothly, and nothing seemed out of the ordinary. When he insisted on driving me home, he framed it as courtesy rather than pressure. He didn’t try anything inappropriate, didn’t linger, and left with a friendly goodnight.

For once, I felt hopeful—a feeling that had become rare. But that optimism vanished the next morning when I woke up to a payment request on my phone. He had sent me a detailed invoice for “expenses,” including gas, parking, and even a fee for “vehicle wear.” I laughed in disbelief before sending him more than he requested along with a note politely stating that I did not wish to see him again. I later learned he had a history of billing women after dates, treating kindness like a service and courtesy like a financial transaction.

Several women online shared similar stories, turning the situation into a viral discussion about dating expectations and emotional labor. The more I read, the clearer it became that his behavior wasn’t a quirky misunderstanding—it was a pattern. In the end, the experience taught me an important lesson: genuine respect doesn’t come with a price tag. A kind person doesn’t tally up basic decency or turn dating into an invoice. I kept my boundaries, retired my brother from matchmaking duties, and filed this bizarre chapter away as a story that still makes people laugh—and shake their heads.