Move Over Hinge And Tinder, Billionaire Bill Ackman’s One Sentence Dating Strategy Is Here To Save Everyone’s Love Life, Provided You Are Also A Billionaire

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. I would ask:  “May I meet you?” before engaging further in a conversation. I almost never got a No. It inevitably enabled the opportunity for a further conversation. I met a lot of really interesting people this way. I think the combination of proper grammar and politeness was the key to its effectiveness. You might give it a try. 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.

Noted ladies' man and billionaire, Bill Ackman, logged on to twitter over the weekend to tell young men how to talk to women, and, as often happens when a billionaire dispenses life lessons, it sounded less like advice and more like a museum audio guide from another century. 

When a cocksman like Bill dishes out love tips, you just know things are going well.

Ackman, a guy who has literally never had to split an appetizer, decided to offer guidance to the unwashed masses of single men on social media. His revelation was that the key to modern romance is a single, elegant sentence. Not therapy, or better workplace policies. Not systemic anything. Just walk up to a woman in public and say, with great poise, “May I meet you?”

As if dating were a Jane Austen novel that had a baby with CNBC.

According to his tweet, this is what he did with his now-wife. He saw her, he asked “May I meet you?”, and she said yes. The article that dutifully rounds this up notes that he delivered the line in a calm, respectful way, no pressure, good eye contact, all the things your HR training video would want from a male protagonist.

In a world where people are burnt out, terrified, and mainlining situationships like they are prescription meds, our latest savior is a hedge fund billionaire who thinks the solution is that single sentence.

And he showed his math and provided some context- 

Ackman’s story is simple. 

He saw a woman he liked, walked over, delivered his killer, “May I meet you?”, and she said yes. 

They are now married. 

It’s a charming little story if you don’t think about it for more than twelve seconds. After that, it starts to sound less like dating advice and more like a billionaire insisting that the way to cure climate change is to open a window.

Ackman frames this like a lost art of masculine courage. Men today, he implies, are hiding behind apps instead of doing what he did- walking across the room, accepting the risk of rejection, and politely shooting their shot.

It is presented as a parable of courage and chivalry, like he stared down the fear of rejection and was rewarded by the universe. The subtext is not subtle- young men today are lonely because they are too glued to their phones and too scared to do what he did. Just grow some balls, guys. 

(I realized this first hand this past summer and blogged about it here)

In Bill's world, if you just remember your pronouns and your please-and-thank-yous, the world will open its arms.

Meanwhile, back on Earth, we have a very different picture.

Picture some poor 26-year-old who just got his rent raised again, lost ten matches to the Hinge algorithm, and is now listening to a hedge fund billionaire explain how to cold approach like it is the Sermon on the Mount.

“My guy, I am eating Costco rotisserie chicken over the sink. I cannot afford to ‘May I meet you’ anyone.”

The line itself is perfect in its absurdity. It sounds less like flirting and more like a suitor in a Victorian parlor asking a father for permission to court his daughter while a butler polishes the silver. 

The man is worth billions of dollars and logged on like a relationship podcaster with a ring light to tell regular people, living paycheck to paycheck, how to talk to women in Whole Foods. 

You have to admire the confidence. And how oblivious he is.

Most of us think “modern dating” and think, yeah, this is a mess of apps, porn brain, anxiety, debt, roommates, and people who think “what are we” is a hate crime. Ackman apparently looks at the same disaster and thinks, “This feels like a phrasing issue.”

It is incredible how often rich guys confuse “this worked for me in a completely rigged environment” with “this is scalable advice for the general population.”

No one who has ever taken a 2 a.m. Uber home from a failed "situationship" or whatever the kids are calling them these days, and is asking to be “met.” 

They are asking to not be murdered, not be ghosted, and if the universe is feeling extra generous, maybe be texted back without being sent a 47-minute voice note about “not being ready for a label”. 

The funniest part is how he delivers it like he is some relatable dating content creator.

You know the exact type. Soft ring lighting, concerned voice, “Fellas, here is what you need to do.” 

But instead of being some guy in a hoodie with 4K followers on TikTok, it is coming from a man who can move markets with a sentence. The podcast bros are at least pretending they are in the same economy as you. Ackman is recording from another planet.

Normal people are not living in that environment Billy boy. 

Regular dudes are not approaching women in a hedge fund gala while a string quartet plays Coldplay. We are in Target. Or in line at Dunkies. Or they are on the train. They are three unpaid internships and two layoffs deep, trying to remember which dating app they met which person on.

Ackman’s version of reality is- everybody’s on their phone, so just be bold and break through it. 

The actual reality is- everybody’s on their phone because everything in the world is on fucking fire, and the phone is the only place that at least pretends to have filters, blocks, and exits.

I say we tru this experiment. Let's put Bill Ackman in a plain t-shirt, hide the net worth, and drop him on a crowded subway platform in NYC. 

Have him walk up to three different women trying to get home after work and hit them with his golden “May I meet you?” 

And let's see how many of them melt into the rom-com fantasy playing out in his naive mind, vs. how many give him the look that says “I swear to God if this man follows me onto the train I am pepper-spraying him.”

Context matters amigo. Money matters. Power matters. Like the Lox and Lil Kim told us- first you get the money, then you get the power, then mother fuckers respect you. 

But billionaire brain never quite accepts that. Billionaire brain hears “Wow, this situation is really tilted in your favor,” and translates it as “My personal vibe is incredibly powerful and universal.” So he pops onto social media and serves it up like inspirational content for the grindset crowd. 

Bonkers.