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

My best friend assured me that Eric, her boyfriend’s friend, was a gentleman, and our first date seemed to prove it. He arrived with roses, gave me a small engraved keychain, and paid for our dinner without a second thought. I went home convinced it had been one of the best dates of my life.

The next morning, my phone buzzed with a message from him. But instead of a sweet text, I opened it to find a formal invoice titled “Date Night Invoice—Amount Due.” He had itemized “charges” for everything, from the flowers to pulling out my chair. The payment he expected for covering the bill? A guaranteed second date.

I immediately showed the invoice to my best friend, Mia, and her boyfriend, Chris. Chris found it both absurd and hilarious, so he created a parody invoice of his own, charging Eric for “introducing him to a wonderful woman” and “not posting about it online.” After we sent it back to Eric, who tried to explain he was just “setting expectations,” I simply replied with a thumbs-up emoji and blocked him.

What began as a frustrating experience quickly became a funny story we would tell for years. The whole incident taught me a new dating rule: if someone insists on paying, you need to make sure it’s out of kindness and not because they plan to send you a bill afterward. I even kept the keychain, not as a romantic memento but as a souvenir from the most unusual date I’ve ever had.

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