I went on a date with a guy my friend set me up with. He showed up with flowers (not a grocery store bunch, actual roses). Dinner was perfect. He was charming, opened doors, and pulled out my chair. When the check came, I reached for my wallet. Big mistake. “Absolutely not,” he said, sliding his card down. “A man pays on the first date.” I walked away thinking it was one of the best first dates ever.
That was until the next morning when I saw that he’d sent me a Venmo request.
Not as a joke. Not with a funny caption. Just a plain request for $48.50 with a little wine glass emoji next to it. I stared at my phone for a full minute, wondering if I had somehow opened the wrong app or slipped into another universe overnight.
I showed my friend, expecting her to laugh. She didn’t. Instead, she got weirdly quiet and said, “Wait… he did that to my coworker too.”
Apparently, this guy had a whole system. He’d act like some old-fashioned gentleman, insist on paying, and then send women payment requests the next day—sometimes with “Had a lovely evening :)” attached, like that made it better.
So I declined the request and sent one of my own for $48.50 labeled: “Emotional damages for false advertising.”
He blocked me five minutes later.
My friend never set anyone up with him again—and honestly, that was the cheapest lesson he could’ve paid for.
