My Date Insisted on Paying the Bill – I Wish I Hadn’t Let Him

When my best friend Mia set me up with Eric, she swore he was a total gentleman. And at first, she seemed right. Eric showed up to our date with roses and a thoughtful gift — a keychain engraved with my initial. He paid for dinner, opened doors, kept the conversation engaging, and ended the night with a respectful hug. I genuinely thought I’d lucked out.

The next morning, I expected a sweet follow-up text. Instead, I got an “invoice” listing everything he’d done — roses, conversation, dinner — with emotional “charges” like hugs, compliments, and second dates as payment. The kicker? A warning: “Failure to comply may result in collections (Chris will hear about it).”

I sent the screenshot to Mia, who immediately showed it to Chris — Eric’s longtime friend. Shocked and amused, Chris crafted a hilarious counter-invoice charging Eric for “wasting a good woman’s time.” We sent it, blocked Eric, and laughed off the absurdity.

Lesson learned: if a guy insists on paying, make sure he doesn’t bill you for it later. And yes, I kept the keychain — as a souvenir from the weirdest date ever.

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