Is it not enough for billionaires to have their billions and all access passes in corridors of power? Now they want to offer dating advice.
Investor Bill Ackman shared his “may I meet you?” pickup line on X over the weekend, while bemoaning how screens and virtual life have impacted physical interactions.
“The online culture has destroyed the ability to spontaneously meet strangers,” Ackman said, unprompted on X.
“As such, I thought I would share a few words that I used in my youth to meet someone that I found compelling. I would ask: “May I meet you?” before engaging further in a conversation.
“I almost never got a no.”
Ackman has a net worth of US$9.2 billion, although he swears the above strategy was working when he didn’t have a nickel to his name.
He met his current wife, Neri Oxman, eight years ago (when he definitely had a large chunk of cash), and they now have a daughter together. He has three children with his first wife, whom he separated from in 2016.
Ackman’s advice has since gone viral, generating millions of views and thousands of shares.
Why? Because it came from a billionaire, who happens to be (at least from his side) in a happy marriage, as if he were one of the few people who had ever cracked such a code.
Ackman also has advantages when it comes to initiating conversations with others, including his enormous wealth, profile, and ability to move markets with social media posts. These attributes don’t necessarily guarantee interest, but they do (in almost all cases) guarantee a massive power imbalance between Ackman and the individual he is hoping to “meet”.
Ackman’s advice also follows the familiar trope we hear from entrepreneurs and successful investors with a public profile: the idea that “I succeeded thanks to this one simple trick, and therefore everyone can too”. But not everyone shares the same characteristics, luck, education and background. The “one thing” success trick isn’t enough for winning big in business, and it certainly isn’t enough for winning big in dating.
Another issue with Ackman’s line and those who seek to sample it in the wild is that women don’t all share the same level of appreciation for pick-up lines and for being approached by strangers. Women are rarely standing or sitting around waiting to meet a man or to be approached by anyone. Many will find it just plain creepy, regardless of whether or not the approacher owns a private jet.
So why does Ackman think the ‘May I meet You’ line works?
He says it could be the combination of proper grammar and politeness, and adds that being in motion seems to enhance the approach’s effectiveness.
“As long as I was on something moving, so an aeroplane, an elevator, an escalator, a subway, something about that increased the vulnerability of it, of it being effective, and it sparks a conversation,” he said.
When asked to respond to the dating advice going viral during a business interview earlier this week, Ackman again bemoaned online culture and the artificial lives people are creating on social media platforms.
“We have a generation of people sitting at home on Twitter, or more likely on Instagram or wherever, looking at people living sort of fake lives,” he said during the interview earlier this week. “The reality is human interaction is critically important.”
He added his concerns about the loss of in-person relationships, leading to greater loneliness and lower birth rates.
It’s here that we must address some of the lack of self-awareness in Ackman’s concerns.
Much of the wealth of billionaires in recent years has been generated by investments made into tech platforms and AI. This uber-rich class has built and invested in social media and AI, including algorithm-driven dating apps and platforms engineered to retain attention and reward the kind of outrage that leads to a breakdown in social cohesion.
There is something especially tone-deaf about an individual moralising about the young people needing to log off their virtual worlds, while sitting at the apex of an economy built to keep people online as much as possible.
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…
— Bill Ackman (@BillAckman) November 15, 2025