Billionaire Roasted After Giving Dating Advice To Young Men By Touting His Truly Awkward Pick-Up Line

“May I meet you?”

No, this is not a pick-up line from your grandfather’s dusty box of love letters. Nor was it penned by Jane Austen, Shakespeare, or even a Bridgerton-era footman who slipped through a cosmic wormhole to rescue modern romance.

Nope, this was billionaire hedge fund manager Bill Ackman logging onto X to offer lonely young men unsolicited dating advice as if he were America’s last functioning courtship expert.

Y’all… America is down catastrophically bad.

Ackman’s November 15 post, which has now surpassed 36.6 million views, lamented how difficult dating has become for young people.

He started off with:

“I hear from many young men that they find it difficult to meet young women in a public setting. In other words, the online culture has destroyed the ability to spontaneously meet strangers. As such, I thought I would share a few words that I used in my youth to meet someone that I found compelling.”

Insert the 30 Rock GIF of Steve Buscemi as a “hip teen” holding a skateboard at a high school, saying, “How do you do, fellow kids?”

Ackman then unveiled the golden line he used to deploy back when Wall Street was still writing off martini lunches as “research and development:”

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

Before we go any further, let’s pause and appreciate the cinematic absurdity of a hedge fund manager—one worth an estimated $9.4 billion, according to Forbes—advising regular, non-yacht-owning Americans on how to flirt.

This is the same Bill Ackman who founded Pershing Square Capital Management, the “activist investor” firm known for high-risk bets, public feuds, and a long history of dragging corporate America—kicking, screaming, and clutching its quarterly earnings—into whatever governance structure benefits him most.

“Out of touch” doesn’t even begin to cover it; this is a man whose idea of “meeting someone naturally” is bumping into a fellow mogul on the tarmac while both their private jets refuel.

And that’s just the financial side. The 59-year-old also enthusiastically styles himself as a public intellectual. He has donated to both Democrats and Donald Trump, a political U-turn with the same whiplash energy as a 1990s rom-com montage.

Most recently, he’s reinvented himself as a full-time conservative influencer, chiming in on everything from campus “free speech crises” to billionaire-solidarity culture wars. It’s the sort of ideological makeover only a man with a $9.4 billion cushion could attempt without requiring physical therapy.

He continued:

“It inevitably enabled the opportunity for a further conversation. I met a lot of really interesting people this way."

For additional context, Ackman has also been married twice: first to landscape architect Karen Herskovitz, with whom he shares three daughter, and then to designer Neri Oxman, whose name has enough elite cachet to be featured on Netflix’s Abstract: The Art of Design.

The billionaire added:

“I think the combination of proper grammar and politeness was the key to its effectiveness. You might give it a try.”

Ah, yes, nothing says foreplay quite like MLA formatting.

And oh, the internet sure gave it a try, but not quite the way Ackman intended:

In his post, Ackman also clarified that his “old school” greeting was meant to be inclusive:

“And yes, I think it should also work for women seeking men as well as same sex interactions. Just two cents from an older happily married guy concerned about our next generation’s happiness and population replacement rates.”

Of course, he mentioned population replacement rates. Nothing says “romance” like a billionaire slipping into a light demographic panic while encouraging you to use polite grammar.

@BillAckman/Twitter

Meanwhile, Ackman was reportedly a guest at a White House dinner honoring Saudi Crown Prince Mohammed bin Salman, seated alongside Elon Musk, Cristiano Ronaldo, FIFA’s Gianni Infantino, and several AI/crypto moguls. Quite the guest list for a man lecturing the public about meaningful human connections.

Because it is impossible to mention Mohammed bin Salman without mentioning the murder of Washington Post journalist Jamal Khashoggi, we must acknowledge the context: the CIA concluded in 2018 that the crown prince personally approved the assassination.

This is the geopolitical backdrop for Ackman’s nostalgia-infused plea for “proper grammar” in dating — a billionaire dispensing Victorian pick-up lines between war-crimes-adjacent banquets.

And the internet was not done with him:

But here’s the thing: billionaires love treating structural problems as personality flaws, preferably in ways that never implicate themselves. Wealthy men like Ackman live in a bubble where “online culture ruined dating” is a legitimate diagnosis.

At the same time, the actual chokeholds on young people’s romantic lives are wages, rent, climate dread, political instability, and the creeping suspicion that billionaires are captaining the ship straight into the iceberg.

College journalist Nicholas Sherwood captured this dynamic perfectly in Psychology Today:

“If the public is to seriously confront the growing crisis of loneliness, it cannot—must not—frame the crisis as something exclusive to men. To do so is to allow the manosphere to take ownership of the matter and entrench culture further into a contemptuous, misogynistic fugue.”

In other words: loneliness isn’t a male issue, or a female issue, or a “rich man wants to feel wise” issue. It is a human issue—one that will not be fixed by hedge-fund courtship scripts, billionaire nostalgia, or demographic anxiety disguised as dating advice.

Still, if you ever find yourself at a party with Bill Ackman—perhaps one where Elon Musk is passionately explaining Mars colonization to a houseplant—you’ll know exactly what to do. Just walk up, place a hand over your heart, and say with the purest, most grammatically sound diction you can muster:

“May I… log off?”