The Love Guru

In his books, bestselling author Malcolm Gladwell has dissected many inspirational underdog victories, but his own triumph over the opposite sex could well be the most inspirational of all.

Bernard Weil, Toronto Star / Newscom

Eight years ago, on a balmy night in New York's West Village, a darkly beautiful history grad was having a date with a 38-year-old writer. He was a little goofy looking and gesticulated a lot, but he was sweet and had theories about a million things, especially her. He was particularly interested in what made her special. When she revealed a passion for acting, he had a theory about that, too, and how to make it more special.

They drank some wine. They talked some more. He fluttered his long, slender fingers. He seemed so comfortable in his own skin, so authentic. He had this eerie feline self-assurance, and it was hypnotic. Forty minutes later, they were back at his place.

In his books The Tipping Point, Blink, and Outliers, bestselling author Malcolm Gladwell has dissected many inspirational underdog victories, but his own triumph over the opposite sex could well be the most inspirational of all. Since moving to New York in 1996, he’s cast his net wide and deep to amass a staggering tally of conquests. There’s been the poetess, the psychotherapist, the photographer, the filmmaker, the fact checker, the writer at The New Yorker, the bisexual literary siren....

The tall blonde he took to Bar Blanc last December was so smoking hot, an eyewitness wrote that Gladwell “made all the guys in the restaurant want to write their own New York Times bestsellers!”

And these are seriously attractive women, too. The tall blonde he took to Bar Blanc last December was so smoking hot, an eyewitness wrote that Gladwell “made all the guys in the restaurant want to write their own New York Times bestsellers! It the high-school geek landing the prom queen—so wrong, yet so right. “

Gladwell the master boulevardier has in effect become his own outlier, a statistical anomaly too great to ignore. So I set off—in the true Gladwellian spirit of pragmatic inquiry—to examine his amazing transformation from dorky scrivener to epic ladies man.

Growing up in rural Canada, things were not promising for the young penman. Despite loving parents, he was the classic loner who preferred toys to socializing. “I was not a joiner,” he wrote in a family memoir. At Trinity College at the University of Toronto, he was even more socially maladroit. He assumed the pose of young Republican and put a poster of Ronald Reagan on his wall. His friends were no help, either. “We were too nerdy to party,” he has said.

Nine years at The Washington Post did wonders for his professional confidence, and he discovered the social side of reporting. But romantically, there was still no indication of the jungle-maned Casanova to come. “He was kind of nondescript,” recalls a former co-worker who turned down a dinner date.

Then, in 1996, to use a favored Gladwellism, came the moment that changed everything. In a seismic collision to rival Bill Gates discovering his first computer, or Wayne Gretzky getting his first hockey stick, Gladwell moved to The New Yorker.

The magazine’s tony mix of intellect and bohemian chic was the perfect home for Gladwell’s innate quirkiness. His obsessive theorizing was no longer weird. It was intriguing and exotic. Out went the sleeveless V-necks; in came the Nikes, jeans, and artfully untucked shirts. He got a pad in Tribeca and alighted on his signature prop—the mad-professor afro. The prototype was Albert Einstein, who was no slouch with women himself. But Gladwell modernized the look with a shoulder bag and turned himself into a local fixture, toiling over his laptop in cafes and restaurants. He went to book launches, magazine parties, and nightclubs, and enjoyed park-bench picnics.

He became a published author and hit the publicity circuit, which gave him the necessary practice hours to hone his knack for yarn-spinning.

On stage, he can keep a packed auditorium totally spellbound with his dilatory talks that weave together Fleetwood Mac, Fermat’s Theorem, and contemporary design. Over a health-food meal for two, it’s even more seductive. Friends have a phrase for the bachelor maestro’s pixie-dust magic: They call it having “Malcolm powder” sprinkled in your eyes.

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But stimulating conversation, however silky, only gets you so far. In any seduction, there is the moment on the sofa or doorstep when subtext becomes text, when intentions have to become clear and a decision made, one way or the other—the Schtupping Point.

There is a range of opinion among Malcolm’s seraglio on how the master handled this pivotal moment.

“It was seamless. One minute you’re walking along; the next you’re arm in arm.”

“Hmmm. How long ago was that? It wasn’t some slick move, if that’s what you mean. Just very normal, very sweet. He’s a runner, you know. Trim as a bird.”

Clearly, it was time to talk directly to the great man himself. I was excited to share my discovery with Gladwell that a French psychology professor, Nicolas Gueguen, had conducted experiments in the area of seduction, specifically the art of making the first move. Gueguen found that a light touch on the arm when asking for a phone number gave men a 9 percent higher success rate than an approach with no physical contact. When asking for a dance, the success rate was 22 percent higher. Surely, I thought, this same principle could be applied even more effectively to the pivotal sofa moment.

I tracked down Gladwell on his cellphone, amid the hum of coffeehouse chatter, and outlined my thesis. He was very polite and completely mortified. “This is ridiculous. Why would I want to talk about such a thing?”

Discretion, it goes without saying, is the cornerstone of long-term success in the amatory arts. But I did think some mild theorizing on a beloved topic would prove irresistible to Americans’ alpha mind. I wove together Gueguen’s findings, the rise of the literary rock star, and the importance of iconic hair all in one sentence, and still I hit the wall.

“This is utterly ridiculous. I mean, I don’t know you. How would you know such things?”

I didn’t panic or give up. Like any good outlier, I simply switched to the full court press.

“So, Malcolm, what can you say about the importance of context for any aspiring ladies’ man? How tough is it, for example, to engineer romance wearing a knitted tie in a hard-nosed newsroom?”

As he would put it, this was my Disqualifying Statement, and not just a mild one, either.

“I write books. I’m a private person.”

I tried to say his success with women was a tribute to the fact that he embodied his own principles for late bloomers (10,000 hours of practice minimum!); that he gave hope to lovelorn dweebs everywhere. But it was too much, too late.

”No, no—I don’t think I want to participate in this at all,” said Gladwell decisively, before signing off with his trademark upbeat ending: “But good luck with it!”

I now realize that I should have trusted my initial gut instinct and invited him for help. I tried to impress him, you see, when I should have just been sincere. In effect, what I did was lunge and force the issue, thereby ruining the mood. And that, in a nutshell, is the difference between the novice and the grand master.

Sean Macaulay was the L.A. movie critic for The London Times from 1999 to 2007. He has also written for Punch, British GQ, and The Mail on Sunday. He was most recently creative consultant on the award-winning documentary Anvil! The Story of Anvil.