You Don't Need a Better Pickup Line. You Need a Better Life.

Billionaire hedge funder Bill Ackman has been mocked on X for advising young men struggling to find a date to go up to a woman in public and simply say: “May I meet you?”

Claiming that he found success himself with this technique, Ackman added: “I think the combination of proper grammar and politeness was the key to its effectiveness. You might give it a try.”

Some felt his advice was hopelessly naive and unrealistic. But at a time when 45 per cent of men aged 18 to 25 have never asked a girl out in person, he should be applauded for offering some kind of solution to our current crisis. Increasingly, we are seeing a generation of “lost boys” opting out of education, employment, marriage and fatherhood, in favour of more dystopian pursuits, often found online.

Scott Galloway, an NYU professor, investor and podcaster, published a bestselling book this month, Notes on Being a Man, which highlights the problem and encourages men to “get out of the house”, “take risks” and “don’t let rejection stop you”.

I would add another piece of advice to this list for my fellow men: be interesting.

Being interesting means creating a spark in the other person’s mind. It can come from telling a good story, teasing in a playful way, dancing well or making the other person laugh. When I lived in England, my barber was fond of saying that all you needed for a woman to like you was “a good chat”.

The trouble is that many men struggle with basic conversation. They cannot show their strengths in a natural or appealing way. They lack experiences worth talking about. Their daily life gives others nothing to admire or be curious about.

So you have to work on two fronts.

First, learn how to talk to people in general, not just women. Too many young men ask how to talk to the opposite sex, which skips over the more basic skill. You need to learn how to talk to human beings. Speak with your friends more often. Spend more time around other people. If the only person who will talk with you is your mom, then start there. The point is to become comfortable speaking, listening, and responding. Before you learn how to talk to the opposite sex, you need to learn how to talk to people in general. If you won’t talk to the Uber driver or your barber, you’re never going to turn into Casanova and meet the woman of your dreams.

Conversation is a skill like any other. And just about everyone, regardless of their intelligence or personality style, can improve on this skill.

Second, you need to build yourself into someone who is genuinely interesting. When you meet someone new, offer small pieces of who you are, but do not rush to give your entire story. Leave room for curiosity. Let them ask the next question.

Living a more varied and active life makes this easier. When you go out into the world and do real things, you naturally develop stories, details and insights that become conversational hooks. These small pieces draw people in.

Two days ago, the comedian Adam Carolla was on Joe Rogan’s podcast. Here I’ll paraphrase one of Carolla’s most important points from this discussion:

“I realised that you have a skill set. Like martial arts. You know it, you’re comfortable with it, you’re secure in it. You know your abilities there, just like you know your abilities as a comedian or as an archer.

For me, I’m a carpenter. I have a skill, a trade. There are things I know well, so I don’t feel insecure. I know what I’m good at, and I’m grounded in that.

But a lot of people don’t have that. They don’t have a trade or a skill or anything they can honestly call expertise. If you asked them, ‘What are you an expert at?’ they wouldn’t have an answer. You could name several — UFC, mixed martial arts, jiu-jitsu, podcasting, standup, whatever it is.

You could learn another language or master an instrument. But so many people never find that thing. They never develop a skill they can own. And because of that, they walk around in this heightened state of insecurity.”

If your life is dull and uneventful, if you spend most of your unstructured time scrolling social media, you will struggle to elicit interest from other people.

This obviously will take some effort. The journalist Derek Thompson recently pointed out that between 1965 and 1995, the typical adult gained 6 hours per week in leisure time. They could have used those additional 300 hours a year to learn a new skill. Instead, the typical American spent nearly all of this extra time watching more TV.

Today, a lot of leisure time is spent scrolling. Put your phone away and learn something.

The good news is that almost everyone has at least a few interesting things to talk about. Or could learn something within reach that will make them more interesting. Cooking, travel, sports, books, languages, side projects, car repairs, music lessons. These small pursuits give you material for real conversation. If your main hobby is digital consumption, you will drain your life of anything worth mentioning. So avoid that trap.

Being cool is different from being interesting. It is less about what you do and more about what you avoid doing. It starts with getting rid of awkward habits and tics and weird body language. It’s mostly about having a calm and steady presence that draws people in. This is harder to teach. You can tell a guy not to lean in too much or not to slump in a way that projects uncertainty, but those are only the first steps. The rest comes from confidence, and confidence grows slowly. A lot of it comes from mastering a skill.

When young men search for the perfect opening line, they are trying to imitate being interesting. Or being cool.

“May I meet you?” is not cool — but it is kind of interesting. Still, the line itself doesn’t really matter. I respect the young guy who actually goes out and tries something far more than the one who mocks from the sidelines.

Rejection is the norm. It’s a cliché, but really it’s not personal. Something like 60 per cent of women under 40 are married or in a committed relationship. If you talk to ten women, six will be unavailable. Of the remaining four, two will decide you are not their type. That leaves maybe two who might be open to meeting you. Most of what happens early on has nothing to do with your worth as a person.

I have been talking here as if people meet each other in person, but most dating now happens on apps. On apps your opener matters even less, because almost everyone makes decisions based on appearance first. On an app, “May I meet you?” can work if she already finds you attractive.

So focus on what you can control. Improve your grooming and hygiene. Get a proper haircut. Stay in shape. Buy clothes that fit your body. Take good photos. It might be worth hiring a professional photographer. You want all the wind at your back. Don’t be embarrassed to make an effort. I promise, it will make you more interesting to others.

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This article was published by the Times of London under the title “Can this four-word pick-up line fix young men’s dating woes?” It is a modified version of a Substack essay I shared last week.