Bill Ackman’s old-fashioned dating advice goes viral but backfires spectacularly

Billionaire hedge fund manager Bill Ackman has sparked a viral storm with some unexpected dating advice he shared online.

The 58-year-old founder of Pershing Square Capital Management, who is worth an estimated $9.3 billion, offered what he said was “old-fashioned wisdom” for young men struggling to meet women in person.

In a post shared on X, Ackman showed concern about what he views as a cultural shift that leaves young men isolated and feeling hesitant to approach women offline.

“As such, I thought I would share a few words that I used in my youth to meet someone that I found compelling,” he wrote.

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“I would ask: ‘May I meet you?’ before engaging further in a conversation.”

Ackman also said the polite phrasing and “proper grammar and politeness” made his approach surprisingly effective, claiming it “almost never got a No.”

He added, “Just two cents from an older happily married guy concerned about our next generation’s happiness and population replacement rates.”

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While Ackman may have intended his words as mentorship, the internet quickly made them a laughing stock.

Thousands of users across X transformed “May I meet you?” into a meme, pairing the phrase with images of awkward party encounters and uncomfortable exchanges between men and women.

One viral post featured comedian Shane Gillis staring creepily into the camera, while another showed a man awkwardly gazing at a group of women at a party.

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One user joked, “May I meet you first thing Monday morning to talk about your performance improvement plan?” above a photo of a smiling woman, which was a playful jab at the line’s stilted formality.

Ackman’s advice arrives amid his growing prominence outside the financial world.

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Ackman married designer Neri Oxman in 2019 after divorcing his first wife, landscape architect Karen Herskovitz. (Patrick McMullan/PMC/ Getty)

Known for his outspoken commentary, he has become a prominent MAGA donor and an influential voice in conservative circles.

His firm, Pershing Square, which manages roughly $16 billion in assets, is one of Wall Street’s most closely watched hedge funds, with Ackman famous for high-profile bets on companies like Chipotle and Herbalife.

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Ackman married designer Neri Oxman in 2019 after divorcing his first wife, landscape architect Karen Herskovitz, with whom he shares three daughters.