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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