When he insisted on paying for our first date, I thought I’d met a rare, old-fashioned gentleman. He brought roses, a thoughtful gift, listened closely, and carried himself with effortless charm. I went home smiling, convinced I’d just had one of the best first dates of my life.
The setup came from my best friend, who swore he was perfect for me. Her boyfriend vouched for him too, which mattered—he was usually right about people. The photo looked promising. Calm. Polished. Reliable. We texted briefly, then met for dinner at a nice Italian place by the river.
He arrived with a bouquet of real roses and a small, personalized gift: a silver keychain engraved with my initial. Dinner was easy and warm. He remembered details, opened doors, pulled out my chair, and paid without hesitation. When I offered to split the bill, he shut it down firmly. Something about it felt off—but I ignored it.
The next morning, he sent me a message with an attachment.
It was an invoice.
Itemized. Professional. Serious.
The roses required a hug. The gift required a coffee date. Opening my car door required a selfie. Paying for dinner required a second date—no excuses. At the bottom: Payment expected in full. Failure to comply may result in escalation.
I blocked him immediately.
What shocked me wasn’t the audacity—it was the belief that kindness was transactional. That decency came with terms.
I kept the keychain as a reminder: charm without sincerity is just performance, and generosity with conditions isn’t generosity at all. Now, when someone insists on paying, I smile—and make sure I know exactly what they think they’re buying.
