After being single for a while, I stepped into a new date with cautious optimism. My best friend Mia had set me up with Eric, a man she swore was sweet, thoughtful, and a true gentleman. Mia’s boyfriend, Chris, backed her up with his own glowing endorsement, so I figured—why not give it a chance? Eric’s photo showed a bright smile and kind eyes, and after a few lighthearted messages, I agreed to meet him for dinner.

Eric made a stunning first impression. He arrived right on time, holding a bouquet of roses and a small personalized keychain engraved with my initials. It felt thoughtful, almost old-fashioned. Throughout the evening, he checked every box: opening doors, pulling out my chair, listening intently, and picking up the bill without hesitation. Conversation flowed effortlessly. We bonded over true-crime podcasts, traded documentary recommendations, and laughed over our shared love for obscure indie films no one else ever seemed to appreciate. When the night ended with a warm, lingering hug, I drove home feeling lighter than I had in months. Maybe—just maybe—I’d finally met someone genuine.

The illusion didn’t even last twenty-four hours.

The next morning, my phone buzzed with an email from Eric. Attached was a neatly formatted PDF titled: “Date Night Invoice.”

At first, I thought it had to be a joke. But as I scrolled, my stomach dropped.

The document itemized every “act of kindness” from the night before, each with a corresponding “required payment”:

• A hug in exchange for the roses

• A selfie as repayment for pulling out my chair

• A guaranteed second date to cover the cost of dinner

At the bottom, in bold, unapologetic letters, it read:
“Payment is due in full. No refunds.”

I sat there in stunned silence, rereading it twice just to be sure I wasn’t imagining things. Then I forwarded it to Mia. Her response was immediate—and explosive. She sent it straight to Chris, who was so offended on my behalf that he decided to flip the situation on its head.

Within an hour, Chris had created his own mock invoice addressed to Eric. It charged him for “wasting a perfectly good bouquet,” “inflicting secondhand embarrassment,” and “attempting to monetize basic human decency.” The final line was the chef’s kiss:
“Payment due immediately, in the form of a public apology to all women.”

We sent it back to Eric.

His reply came in a rapid-fire string of angry messages, accusing us of being childish, ungrateful, and immature. He finished with a dramatic flourish, insisting I had just passed up a “great guy” and would regret it. That was the moment any lingering doubt vanished. I blocked him without another word.

Mia apologized over and over, mortified that she’d vouched for him. I reassured her it wasn’t her fault—there was no way anyone could have predicted something that bizarre. If nothing else, the whole ordeal turned into a story we still laugh about whenever dating comes up.

Dating is unpredictable, especially later in life. But that night taught me a few important lessons: red flags don’t always wave immediately, boundaries are nothing to feel guilty about, and sometimes the best outcome of a bad date isn’t romance—it’s a hilarious reminder of your self-worth, the importance of walking away, and the comfort of having fiercely loyal friends when things go completely off the rails.