Somewhere in Stanford, California, an undergrad is telling his roommates that he landed a Friday night date because he tried a billionaire’s pickup line.
A man on the New York subway is yelling out that same line to strangers. A woman is planning to stand in Washington Square Park wearing a cardboard sign bearing the phrase.
These are just a few scenes from the weekend frenzy in New York City around Bill Ackman’s four-word piece of dating advice: “May I meet you?”
He posted the line as earnest advice for young men who, in his view, now avoid spontaneous interactions because dating apps dominate their social lives.
“Online culture destroyed the ability to meet strangers,” he wrote on X, in a post that has now been viewed over 26 million times. Ackman, who runs a hedge-fund and is a prolific poster on X, claimed the line “almost never” triggered rejection when he used it as a young man, and that it works best when you are on the move.“You might give it a try,” he added. And the internet did what it does best: devolved into endless discourse. Some people called the line “killer” and “alpha,” while many others – including Ramp Capital’s X account – joked about its formality and parodied it. Some critics argued that Ackman’s confidence came from advantages – his wealth and height (6’3) – that don’t apply to most young men, while others, like economist and blogger Tyler Cowen, agreed with Ackman that even if the line falls flat, it helps get Gen Z men “thinking about meeting women at all.”
