The Love Guru

Bernard Weil, Toronto Star / Newscom 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.

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 was...like 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.