Perhaps you’ve heard the dire forecasts about romance these days. Gen Z is dating less, swiping more, and sounding exhausted by the whole enterprise. Headlines warn of a “sex recession,” a phrase that manages to be both alarmist and deeply unromantic. Apparently, young people are lonely, birthrates are falling, and something—someone—must be done.

Enter Bill Ackman.

Last month, the billionaire hedge fund manager took to X with a piece of advice for young men struggling to approach potential dates in public. His solution was concise, grammatically correct, and—depending on who you ask—either charmingly old-school or wildly out of touch.

“May I meet you?”

Ackman wrote that he used the line in his youth and was “almost never” rejected. The secret, he suggested, was proper grammar and politeness. If romance is broken, perhaps it just needs better sentence structure.

The internet, predictably, had thoughts.

There was something oddly fascinating about watching a billionaire pivot into the role of dating coach. This is a man whose recent résumé includes funding President Trump’s third campaign, leading a very public campaign against Harvard’s former president, marrying the architect and former MIT professor Neri Oxman, and briefly competing in a professional tennis tournament (results… mixed). Now, at 59, he was offering a four-word fix for a generation’s romantic malaise.

Critics pointed out that declining birthrates may have less to do with pickup lines and more to do with rent, student debt, and the cost of child care. Others zeroed in on the phrase itself. “May I meet you?” struck many as stiff—overly formal in a world that now opens with hey or, more often, nothing at all. One writer described it as having a “never-felt-the-touch-of-a-woman aura,” which feels harsh but not entirely unearned.

And yet.

Something curious happened when actual humans tried it.

In Austin, a photographer named Sebastian Salinas decided to test the line on a woman from his 7 a.m. hot yoga class. He delivered it. She stared at him, confused. He panicked, rolled up his mat, and fled—face red, dignity bruised.

A few minutes later, she followed him and introduced herself.

In hindsight, he said, it kind of worked.

That detail has stayed with me. And here’s where I have to admit something slightly uncomfortable.

Ordinarily, I would never take (or share with my daughter) romantic or social advice from a staunch Trump supporter like Bill Ackman. Our worldviews diverge too sharply for that. And yet—annoyingly—he may have stumbled onto something familiar.

Because stripped of its billionaire earnestness, “May I meet you?” is not new at all. It is, in fact, the foundational question behind generations of arranged marriages in India.

The process is almost comically formal. First, you see a photograph—sometimes glossy, sometimes tragically overlit. Then a series of intermediaries step in: parents, aunties, uncles, family friends, professional matchmakers. And at the center of it all is a polite, restrained inquiry that governs the entire enterprise.

May we meet?

Not Are you attracted to her?

Not Could you see yourself sleeping with him?

Not even Do you love her?

Just: may we meet?

That question does an enormous amount of cultural labor. It assumes nothing. It allows for refusal without humiliation. It creates a container where curiosity can exist without pressure, and where interest—if it grows—does so incrementally. It also recognizes something we’ve largely lost in modern dating: that desire doesn’t always arrive fully formed. Sometimes it arrives after tea. After conversation. After observing how someone treats a waiter or speaks about their parents.

Seen through that lens, Ackman’s suggestion stops sounding like a Victorian relic and starts sounding like an old-world structure trying to reassert itself in a hyper-digital age. A reminder that romance, across cultures, has often begun not with sparks but with permission.

Which may explain why, despite the awkward delivery, the line keeps working.

Because whether it’s a yoga studio in Austin or a living room in New Delhi, the question does the same quiet thing: it makes space. For consent. For dignity. For the possibility that something might happen—but also that it might not, and that either outcome is acceptable.

We were never meant to choose people the way we choose takeout. The apps promise abundance but often deliver paralysis. They flatten curiosity, encourage disposability, and make rejection feel both constant and impersonal. In that context, a strange, overly formal sentence—spoken aloud, face to face—does something radical. It slows the moment down. It creates an off-ramp. It allows the other person to say no without having to ghost, block, or vanish.

A 26-year-old actor in Santa Monica put it best. At first, she found “May I meet you?” weird. Jarring. But the more she thought about it, the more she appreciated what it offered: consent. An opening that didn’t presume anything beyond a brief exchange between two people occupying the same physical space.

I don’t think billionaires are the right messengers for fixing modern intimacy. And I don’t believe grammar alone will save us from loneliness. But I do think there’s something quietly radical in approaching someone with humility rather than entitlement—without the expectation that interest is owed, or that rejection is catastrophic.

And maybe that’s the part we’ve forgotten—not how to flirt, but how to ask without demanding.