Billionaire Bill Ackman’s ‘Out of Touch’ Pick-Up Line Advice Prompts Thousands of Comments and Mocking Memes

Billionaire investor Bill Ackman sparked a flurry of reactions online after offering dating advice to younger generations on X (formerly Twitter).

On Saturday, Nov. 15, Ackman — well known for his long threads on the platform — suggested that men who struggle to approach women in public try a line that he said worked for him years ago:

“I would ask: ‘May I meet you?’ before engaging further in a conversation,” he wrote. “I almost never got a ‘No.’”

He added that the combination of “proper grammar and politeness” made the approach more successful and encouraged younger users to give it a try. Ackman, 59, also said the method could apply to women approaching men and to “same-sex interactions,” noting that spontaneous, real-world socializing has been weakened by online culture.

“Just two cents from an older happily married guy,” he said, expressing concern about younger people’s happiness and the declining birth rate.

His post has since been viewed more than 26 million times and generated over 4,000 comments.

One response came from journalist and activist Melissa Chen, who recounted how a man in his 20s recently asked her out. She politely declined — pointing out her engagement ring — but encouraged him to keep trying and advised him on what social cues to watch for.

Others chimed in with their own experiences or questions for the hedge-fund founder. But many pushed back, calling Ackman “out of touch,” with some commenters pointing out that safety concerns make many women wary of being approached by strangers.

Another user jokingly described trying the line at a café, saying he was swiftly banned — humorously framing it as “a common way of playing hard to get.”

Memes soon followed, humorously applying the phrase “May I meet you?” to images ranging from Vice President JD Vance to actress Sydney Sweeney.

Ackman is no stranger to online ribbing. Earlier this year, he teamed up with former tennis pro Jack Sock for a doubles match against Bernard Tomic and Omar Jasika during the Hall of Fame Open in Rhode Island — a match that ended in a lopsided 6-1, 7-5 loss and plenty of teasing from spectators.

Critics resurfaced during this latest round of banter, with one commenter suggesting the line only worked because he’s a billionaire. Ackman replied simply:

“I didn’t have two nickels then.”