My Date Paid for Dinner, Then Everything Took a Turn!

I later reviewed his email one more time, trying to rationally understand his thought process. Was his motive truly about power? Was it purely ego? Or was it just the garden-variety arrogance of an entitled man, poorly disguised as humor? It was probably a combination of all three.

What struck me most was how rehearsed the whole thing felt. The organized layout, the specific wording, the entire fabricated professionalism—this clearly was not a quick, spur-of-the-moment prank. He had almost certainly done this before, or at the very least, had thought about executing this kind of scheme multiple times.

Perhaps he fully expected me to simply laugh it off, or to play along, thereby feeding his desperate need for control, which he mistook for wit. Instead, I did the one thing that truly undermined him: I completely ignored him after my final, simple reply.

In the days that followed, Mia and Chris did the right thing and cut him off completely from their social circle. Apparently, when Chris seriously confronted Eric, he only doubled down on his behavior—claiming that I was “too sensitive” and that “women don’t appreciate humor anymore.” This was a classic, predictable defense mechanism to deflect responsibility.

Meanwhile, my phone remained peacefully and blissfully quiet. There was no more contact from the ‘gentleman’ and no more absurd invoices. Just welcome peace and quiet.

Looking back now, I can almost appreciate the absurdity of the whole ordeal. The evening had started out like a scene from a romantic comedy—all roses, charm, and laughter—but it quickly spiraled into a cautionary, eye-opening tale about the deeper issues of modern dating and a terrible sense of entitlement.

If nothing else, I took away a vital lesson: always pay close attention to the small red flags before they have the chance to grow into massive, life-altering problems. Anyone who views basic courtesy, kindness, or generosity as a debt that is waiting to be collected is not romantic or charming—they are deeply manipulative.

So now, when friends or new acquaintances ask me about my absolute worst dating experience, I don’t even have to pause.

“The one who sent me an invoice,” I say, usually with a big grin.

The story always gets a huge laugh, but I always make sure to add the important punchline: “And he really thought I’d pay.”

The truth is, I did pay a price that night—just not in the way he fully expected. I paid attention. And that valuable awareness is worth far, far more than any dinner bill.