My Date Picked Up the Tab—Then Sent an “Invoice”: A Modern Dating Red Flag You Shouldn’t Ignore

I’ve been on enough first dates to know that a polished start doesn’t guarantee a happy ending. Still, when my friend Mia urged me to meet a colleague of her boyfriend’s, I decided to give it a try. She sang his praises: polite, smart, dependable—the kind of “gentleman” that, in theory, makes modern dating feel hopeful again. Given her confidence, I said yes.

From the beginning, Eric checked the right boxes. He texted in full sentences, asked thoughtful questions, and suggested a reservation at a respected Italian place downtown. It sounded promising—a welcome change from the half-hearted, last-minute “you up?” culture. If you’re keeping score of dating red flags, there weren’t any yet. In fact, it felt like the beginning of a sweet story, not a cautionary tale about entitlement or a first date invoice.

A Polished First Impression

He arrived early, holding a small bouquet and wearing a crisp button-down. He opened doors, pulled out my chair, and complimented my dress without being smarmy. Even the gift he brought—a tasteful keychain with my initial—felt thoughtful rather than flashy.

Our conversation was easy. We talked travel and work, the shared comedy of terrible app experiences, and the loss of old-school movie theaters you could enjoy without taking out a small loan. When the check arrived, I reached for my wallet out of habit.

Eric waved me off. “I’ve got it,” he said, sliding his card to the waiter with a practiced flourish. Old-fashioned, perhaps, but generous. I didn’t argue.

Outside, he offered his arm, walked me to my car, and waited until my engine turned over before heading to his. No pushy invitations, no lingering awkwardness—just a clean, pleasant goodnight. Driving home, I texted Mia: You might be right about this one.

The Morning Curveball