The Ultimate Troll: The Terrifying Allure of Gamergate Icon Milo Yiannopoulos

Perhaps the most shocking thing about Milo Yiannopoulos is that he is utterly charming.

Online, the 31-year-old conservative Breitbart columnist is the sort of frustrating troll who, for instance, might declare his birthday World Patriarchy Day, suggest Donald Trump is “blacker” than Barack Obama, or, although he is gay himself, assert that gay rights have “made us dumber.”

He was recently booted from a demonstration against sexual violence in Los Angeles after showing up with a sign that read “‘Rape culture’ and Harry Potter. Both fantasy.” A dedicated contrarian, Yiannopoulos seems to delight in making enemies.

But in real life — in spite of all this, or, perhaps, because of it — Yiannopoulos is disarmingly likeable. After all, you don’t amass 85,000 Twitter followers, become the conservative torch-bearer in a gaming industry civil war, attract a cult following among young, Internet-savvy men, and become a figurehead of the Men’s Rights movement without knowing a little something about exploiting the human psyche.

When I meet him in San Francisco, a few days after the aforementioned demonstration, he greets me as if we’re old friends.

“Hello darling, how are you!” he exclaims, offering a hug. Yiannopoulos, who lives in London, was once described as a cross between a “pitbull and Oscar Wilde.” It’s barely noon on a Monday, and he and a friend are drinking in a dark bar in the Lower Haight, already onto their second glass of rosé. He had ordered me a glass. Wearing his signature aviators indoors, leisure shorts, white plastic flip-flops and a t-shirt reading #REPUBLICAN in gold foil lettering, Yiannopoulos looks slightly hung over.

We discuss his favorite American president (Calvin Coolidge, for his wit), George W. Bush (“incredibly sexy in person”), his belief that there are fewer transgender men than women (“women don’t care to become men”) and his searing hatred of third-wave feminism, which Yiannopoulos characterizes, generally, as a mob of bitter man-haters railing against institutional injustices like the wage gap that no longer actually exist.

“I would be a second wave feminist,” he says. “I believe in equal opportunities for women, but if they don’t choose to work as hard, they don’t get rewarded.”

“I don’t think you know what feminism means,” responds his drinking companion, a liberal lawyer, who tells me that she blocked Yiannopoulos on Facebook because she sometimes finds his columns so infuriating. This, it turns out, is common sentiment among many of his friends.

“I just can’t believe you’re anti-feminist!” she tells him.

“I would never describe myself that way,” he responds, launching into a much-rehearsed soliloquy. “There is a specific brand of feminism that is destructive and I think it is driving men and women apart. I hate it. It makes everybody miserable.”

Their friendship survives, she explains, because they generally agree not to discuss topics like politics.

“People have this idea that I’m a misogynistic monster,” Yiannopoulos tells me, “But as soon as they meet me they say, ‘Oh, you’re so nice in person!”