Billionaire Bill Ackman offered young men advice on approaching women in public, prompting a wave of online mockery.
The pro-Trump CEO of Pershing Square Capital Management, who has a net worth of $9.4 billion, shared “a few words” that he claimed have never gotten him a no from women.
“I would ask: ‘May I meet you?’ before engaging further in a conversation,” Ackman, 59, said of the pickup line he used in his youth, and the internet was quick to react.
“I tried this at the coffee shop. I asked this cute girl sitting next to me, ‘May I meet you?’ She said no. The end,” one user shared on X alongside a GIF depicting a noose, to which the 59-year-old replied, “Try again. You need not fear being rejected. Wrong girl for you. Her loss, your gain.”
Another user shared a screenshot of trying the line in a modern context on a dating app, receiving no replies from the five women he messaged with Ackman’s phrase, which the billionaire had praised for its “combination of proper grammar and politeness” as the key to success.
The former Democratic donor, who has since become a MAGA enthusiast, married his first wife, Karen Ann Herskovitz, 59, in 1994. The couple divorced in 2017 and shares three children.
According to one of Ackman’s posts, he was first introduced to his second wife, designer Neri Oxman, 49, by a friend after he and his ex-wife emailed their friends about their separation. The billionaire explained that Oxman had a boyfriend at the time, and they went on their first date only when they were both “out of relationships.”
Many social media users pointed out that Ackman’s dating strategy may be out of touch, considering his wealth.
One user posted a photo of King Charles III dressed in full golden royal gowns and crown, captioned “Dudes preparing to unleash their Bill Ackman–approved pick-up line at the club tonight.” Another wrote “‘May I meet you?’ he billionaired softly.”
Dudes preparing to unleash their Bill Ackman–approved pick-up line at the club tonight.
“May I meet you?” pic.twitter.com/RaErfFeUpA— Daniel Sempere Pico (@BTCGandalf) November 16, 2025
“I tried this on random women: One stared at me saying nothing, one said she had a boyfriend, one said ew,” one user complained about their failed attempt at Ackman’s flirting style, adding, “What do I do now Bill? Pull out my amex black card?”
Despite Ackman’s confident advice to young men, the billionaire has previously admitted that he was once scared his current wife, then his girlfriend, would leave him for Brad Pitt after the actor visited her workplace and there was a “radio silence” from her.
Some online users pointed out that Ackman’s line is off-putting, with one person writing that if the “creepy line” didn’t scare a woman away, “she’s definitely not my type,” while another captioned a photo of former President Barack Obama looking through a magnifying glass with, “Me looking for a cringier post. Can’t find.”
Me looking for a cringier post. Cant find pic.twitter.com/2LxxpaqtpY
— Son of Anders (@Son__of__Anders) November 15, 2025
A November Gallup poll showed that 40 percent of women want to leave the U.S. permanently, twice the share of men who feel the same.
“Just two cents from an older happily married guy concerned about our next generation’s happiness and population replacement rates,” Ackman concluded his now-ridiculed post on X.
The Daily Beast has reached out to Ackman for comment regarding the reactions to his posts.
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