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The Night I Realized Letting My Date Pay Wasn’t Such a Good Idea

Posted on August 25, 2025 By author author No Comments on The Night I Realized Letting My Date Pay Wasn’t Such a Good Idea

When my best friend Mia set me up with her boyfriend’s friend Eric, she promised he was a true gentleman. And at first, she seemed right. On our first date, Eric brought roses, surprised me with a small engraved keychain, and kept the conversation light and charming. He pulled out my chair, paid for dinner without hesitation, and treated the evening like something out of a classic romance. I went home smiling, certain I’d just had one of the best dates of my life.

The next morning, my phone buzzed with a message from him. Expecting a sweet good-morning text, I opened it—and froze. It wasn’t a message at all but a professionally styled invoice titled “Date Night Invoice – Amount Due.” Line by line, Eric had listed “charges” for every part of the evening: flowers, dinner, even pulling out my chair. And for covering the bill? He had listed “payment” as a guaranteed second date. At the bottom, in bold letters, it read: “Payment expected in full. No refunds.”

I sent it straight to Mia, who showed her boyfriend, Chris. He was both furious and amused, so he made a parody invoice in return—charging Eric for “introducing him to a wonderful woman” (payment: a permanent block) and “not posting about it online” (payment: endless gratitude). We sent it back to Eric, who immediately filled my phone with long explanations about how he was just “setting expectations.” I replied with a single thumbs-up emoji and blocked him.

Later, Mia apologized, but by then we were all laughing about it. What started as a disappointing experience turned into a story we’d tell for years. I also walked away with a new dating rule: if someone insists on paying, make sure it’s out of kindness—not because they plan to send you a bill afterward. As for the keychain? I kept it. Not as a keepsake of romance, but as the funniest souvenir from the most unusual date I’ve ever had.

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