I went on a Tinder date with a guy named David. He said he was 30, but I later found out he was 38. He picked a pretty upscale restaurant and told me not to worry about the bill—he’d cover everything. I still ordered modestly: cheapest entrée, one drink, nothing extravagant. The date itself was fine, nothing particularly memorable or weird. We made small talk, laughed a little, and parted ways politely. I figured that was that. But later that night, I got a call from an unknown number. I answered, expecting maybe a follow-up. Instead, I got his mother.
She introduced herself and said David had come home “very upset.” Apparently, I’d mentioned during dinner that I don’t usually date men much older than me, and that had “hurt his feelings.” She said since I “wasn’t serious about him,” it was only fair that I transfer half the cost of dinner to his account. I was stunned. Not just by the request, but by the fact that his mother was the one making it. I didn’t even know he lived with her, let alone that she’d be calling me on his behalf.
I sat there holding the phone, trying to process what was happening. Was this real? Was I being pranked? But no, she was completely serious. She even gave me his bank details. I didn’t argue. I didn’t explain. I just ended the call, opened my banking app, and sent the money. Not because I felt guilty—but because I wanted to be done with the whole bizarre situation. And I added a note to the transfer: “Buy yourself the most expensive pacifier you can find.”
I don’t know what reaction that got, and honestly, I don’t care. The whole thing was so absurd it felt like satire. I’ve had bad dates before, but this was a new level. I wasn’t even mad—just baffled. Who sends their mom to chase down a dinner bill because their ego got bruised? Who lies about their age and then plays the victim when the truth comes out? I guess David does. And I guess I learned something about trusting my instincts.
Looking back, there were red flags I ignored. The age discrepancy, the over-the-top restaurant choice, the way he insisted on paying but seemed a little too eager about it. I brushed it off, thinking maybe he was just trying to impress me. But now I see it for what it was: a performance. And when the fantasy cracked, he couldn’t handle it. So he called in backup—his mom. I hope she’s proud. I hope he enjoyed his pacifier. And I hope I never hear from either of them again.
So here’s to the weirdest date I’ve ever had. To the moment I realized that emotional maturity doesn’t always come with age. To trusting your gut, even when the wine list is fancy. And to every woman who’s ever had to Venmo a man-child because she bruised his ego. May we all learn to spot the red flags sooner—and may our pacifier fund never run dry.
