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Why Letting My Date Pay Was the Worst Decision of the Night

Posted on August 11, 2025August 11, 2025 By author author No Comments on Why Letting My Date Pay Was the Worst Decision of the Night

When my best friend Mia set me up with her boyfriend’s friend Eric, she promised he was a total gentleman. On our first date, he proved her right—roses, a thoughtful engraved keychain, charming conversation, and unwavering attentiveness. Dinner was perfect, and when the bill came, he insisted on paying with a firm, almost old-fashioned finality. I went home thinking I’d just had one of the best dates of my life.

The next morning, I woke up to a message from Eric—not a sweet follow-up, but a professionally formatted invoice titled Date Night Invoice – Amount Due: 1 Outstanding Balance. It listed “charges” for his gentlemanly acts: a hug for the flowers, a coffee date for the gift, holding hands for pulling out my chair, and, for covering dinner, a guaranteed second date. At the bottom, in bold, it read: Payment expected in full. No refunds. Failure to comply may result in Chris hearing about it. My jaw hit the floor.

I sent it to Mia, who immediately showed her boyfriend Chris. Outraged and amused, Chris made a parody invoice in return—charging Eric for “introducing you to a gorgeous woman” (payment: a permanent block) and “not exposing you to the internet” (payment: eternal gratitude). We sent it to Eric, who responded with a flurry of indignant messages about how he was just “setting realistic expectations.” I replied with a single thumbs-up and blocked him.

Later, Mia apologized, but I couldn’t stop laughing. We’d all gotten a story we’d tell for years—and a personal dating rule I’d never forget: if a man insists on paying the bill, make sure it’s not because he plans to send you an invoice. As for the keychain? I kept it. Not as a token of romance, but as the funniest souvenir from the weirdest date I’ve ever had.

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