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

When Eric insisted on paying for our first date—with roses, a gift, and charming conversation—I thought I’d found a true gentleman. Things started well: Mia, who set us up, and her boyfriend Chris vouched for him. After text exchanges, we met for a nice Italian dinner by the river.

Eric brought a professional bouquet and a personalized keychain engraved with “K.” He opened doors, pulled out my chair, and paid the whole bill, insisting proudly, “A man pays on the first date.” Our conversation flowed, we couldn’t stop laughing and sharing interests, and when he hugged me goodbye, I felt optimistic.

The next morning, I got a “Date Night Invoice.” It hilariously charged me for the roses, the keychain, chair-opening, conversation, dinner, and more—with deadlines and threats about collections. It wasn’t a prank—he meant it.

I showed it to Mia and Chris. Chris laughed so hard that he drafted a mock invoice in response—accusing Eric of wasting an opportunity and demanding apologies. Eric lashed out, but I merely blocked him. In the end, Mia apologized for the awkward setup, but we all got a story worth telling. I kept the keychain—not as a memento of him, but as a hilarious souvenir from the most bizarre date ever.