When Eric insisted on paying for our first date, I thought I had met a true gentleman. He arrived with roses, a small gift, and charming conversation. Every romantic comedy cliché was unfolding. My best friend, Mia, had set this up, swearing I’d love him.

I was skeptical but gave it a shot, especially since her boyfriend, Chris, vouched for him. When she sent me Eric’s picture, I had to admit—he was cute. After a few texts, we planned dinner at a cozy Italian restaurant by the river.

Eric exceeded expectations. He greeted me with roses—not cheap ones—and a small, thoughtful gift: a silver keychain engraved with my initial. He pulled out my chair, remembered details from our conversations, and engaged in deep conversation. We shared a love for true crime podcasts and bizarre documentaries.

Then came the check. I instinctively reached for my purse.

“Absolutely not,” Eric said firmly, slapping his card down. “A man always pays on the first date.”

His tone was strikingly final, but I let it slide. He walked me to my car, asked if he could call me, and I genuinely looked forward to it.

The next morning, I woke up to his text—not a sweet message, but an invoice.

DATE NIGHT INVOICE – AMOUNT DUE: 1 OUTSTANDING BALANCE.

The breakdown:

• Bouquet of Roses: 1 hug
• Custom Keychain: 1 coffee date (scheduled within one week)
• Opening Car Door: A cute selfie together
• Pulling Out Chair: Holding hands on the next date
• Engaging Conversation: A compliment about my looks
• Full Dinner + Tip Covered: A second date, no excuses

At the bottom: PAYMENT EXPECTED IN FULL. FAILURE TO COMPLY MAY RESULT IN COLLECTIONS (CHRIS WILL HEAR ABOUT IT).

My jaw dropped. Was he serious? I immediately sent it to Mia.

Her reply: “OH. MY. GOD. I’M SHOWING THIS TO CHRIS RIGHT NOW.”

Five minutes later, Chris called, howling with laughter. “Kelly, I cannot believe this. This is next-level insanity.”

Chris, the king of pettiness, decided to get even. An hour later, he sent Eric an invoice:

• Introducing You to a Gorgeous Woman: 1 permanent block on all platforms
• Convincing Her You Were a Gentleman: A deep reflection on why you’re single
• Letting You Sit at the Same Table as Her: A formal apology to all women you’ve dated
• Not Exposing You Online: A generous gift you should be grateful for

PAYMENT DUE IMMEDIATELY. FAILURE MAY RESULT IN PUBLIC HUMILIATION. CHEERS!

Eric’s response? Furious texts. “Wow, really mature.” “I was just setting expectations.” “You missed out on a great guy.”

I sent a thumbs-up emoji and blocked him.

As for the keychain? I kept it—as a hilarious souvenir from the weirdest date of my life.