This billionaire’s ‘diabolical’ pick up line has gone viral for all the wrong reasons

In an age of ‘send pics’ and ‘you up?’, the bar for pickup lines is, quite frankly, in hell.

Seeing this sorry state of affairs, one billionaire, Bill Ackman, took to X last week to share his slice of dating advice, including the one pick up line that hardly ever failed him.

But while well intentioned, the internet wasn’t all that impressed with what the hedge fund manager had to offer, branding the advice ‘diabolical’ claiming it was coming from someone who has ‘no real comprehension’ of the dating landscape.

‘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,’ a well-intentioned Bill wrote 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”.’

In the post which has now been viewed more than 33 million times, he claimed this pick up line enabled further conversation and allowed him to meet really interesting people.

‘I think the combination of proper grammar and politeness was the key to its effectiveness,’ he added. ‘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.’

As you can imagine, in a climate where skibidi, gyatt, and no cap are used in daily conversation, people aren’t exactly fussed about the allure of correct grammar.

‘”May I meet you?” What planet are you from? People don’t speak that way today or ever,’ commented Mansa Musa on X.

‘You sound so out of touch lmao “May I meet you” what kind of robot uses that as a pickup line?’ added Lib Dunk.

One even said: ‘I would stick to financial advice Bill. No offence.’

Others felt he already had a bit of an advantage. ‘It helps that you are very handsome Bill,’ X-user Ryan Petersen commented.

‘“May I meet you?” he billionaired softly,’ added Saila.

Some people pointed out that being married for so long meant Bill wasn’t the most qualified to speak on the current dating landscape.

‘What I’ve found is that people who’ve been married for a long time have no real comprehension of how much the dating landscape has changed because of dating apps and social media,’ one social media user wrote. ‘I appreciate your suggestions in a vacuum but they are not practical in 2025.’

Why has Bill’s pick up line been so poorly received?

When taken at face value, Bill’s pick up line is confusing. ‘The formality of the grammar and structure of the sentence leads to it feeling out of context, especially in an environment where young people are used to chatting informally online,’ psychotherapist Eloise Skinner tells Metro.

‘It might not be understood as an invitation to a date, or might even feel like the person asking is being unserious or mocking.’

Charlotte Fox Weber, BACP registered psychotherapist, adds: ‘It sounds like something a duke murmurs before asking for a waltz. It’s archaic, bloodless, and socially tone-deaf.

‘Dating now is all warmth, humour, and immediacy. “May I meet you?” feels embalmed — like a line exhumed from a museum of misguided courtship.’

So let’s be real, would Gen Z ever use this? ‘Not a chance. Gen Z can detect cringe like a cadaver dog,’ Charlotte tells Metro. ‘They want authenticity, not a line that sounds handcrafted by a billionaire who’s never queued for anything, let alone risked real-world rejection.’

Bill’s pick up line also fails to acknowledge how the dating game has evolved since he was trying to find a significant other.

‘We’ve outsourced the early stages of flirting to apps,’ Charlotte explains. ‘It’s made IRL approaches feel almost feral — thrilling but unfamiliar. At the same time, our cultural awareness of boundaries has skyrocketed.

‘You can’t swagger up with false confidence anymore; you need sensitivity, timing, and a sense of the room. People are rusty. Apps trained us to flirt through screens, so the analogue version feels terrifyingly exposed.

‘Add headphones, social fatigue, and the fear of “being that person,” and you’ve got the perfect cocktail of hesitation.’

However, psychotherapist Eloise believes that its memeification online may lend itself to it becoming more usable. ‘Since it’s spread widely across the internet, it might end up being quite a fun or playful opening line,’ she explains.

‘If received in an environment where both people can acknowledge the inside joke nature, it can become a light-hearted way of connecting with someone and might actually feel lower-stakes than asking someone out in other ways.’

What pick up lines should you use instead?

You don’t want to seem archaic, out of date, or creepy, but it can feel like you’re stepping on eggshells. So, we asked for some expert approved options to improve your odds.

‘Sorry to interrupt —this is wildly forward for me, but you seem lovely.’

Charlotte says: ‘This is human. Not slick, not sleazy. It shows nervousness, which paradoxically builds trust.’

‘I’d kick myself later if I didn’t say hello. Fancy a quick coffee sometime?’

‘It’s clear and time-bound. You’re asking for something real, not trapping them in a monologue,’ Charlotte explains.

‘You give off good-energy vibes. If you feel like chatting, I’d be delighted.’

‘Complimenting someone’s energy avoids objectifying them,’ the psychotherapist adds. ‘And “if you feel like” signals freedom.’

‘You strike me as someone who appreciates a good moment of serendipity. Shall we?’

Charlotte says: ‘It invites them into a shared story. It’s modern, whimsical, and low-pressure.’

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