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In 2014, Wynn noticed a trend on YouTube that disturbed her: Videos with hyperbolic titles like “why feminism ruins everything,” “SJW cringe compilation,” and “Ben Shapiro DESTROYS Every College Snowflake” were attracting millions of views and spawning long, jeering comment threads. Wynn felt she was watching the growth of a community of outrage that believes feminists, Marxists, and multiculturalists are conspiring to destroy freedom of speech, liquidate gender norms, and demolish Western civilization

Wynn created ContraPoints to offer entertaining, coherent rebuttals to these kinds of ideas. Her videos also explain left-wing talking points—like rape culture and cultural appropriation—and use philosophy to explore topics that are important to Wynn, such as the meaning of gender for trans people.

Wynn thinks it’s a mistake to assume that viewers of angry, right-wing videos are beyond redemption. “It’s quite difficult to get through to the people who are really committed to these anti-progressive beliefs,” Wynn told me recently. However, she said, she believes that many viewers find such ideas “psychologically resonant” without being hardened reactionaries. This broad, not fully committed center—comprising people whose minds can still be changed—is Wynn’s target audience.

Usually, the videos to which Wynn is responding take the stance of dogged reason cutting through the emotional excesses of so-called “political correctness.” For example, the American conservative commentator Ben Shapiro, who is a target of a recent ContraPoints video, has made “facts don’t care about your feelings” his motto. Wynn’s first step in trying to win over those who find anti-progressive views appealing is to show that these ideas often rest on a flimsy foundation. To do so, she fully adopts the rational standards of argument that her rivals pride themselves on following, and demonstrates how they fail to achieve them

Wynn dissects her opponents’ positions, holding up fallacies, evasions, and other rhetorical tricks for examination, all the while providing a running commentary on good argumentative method.

The host defends her own positions according to the same principles. Wynn takes on the strongest version of her opponent’s argument, acknowledges when she thinks her opponents are right and when she has been wrong, clarifies when misunderstood, and provides plenty of evidence for her claims

for Wynn, the true key to persuasion is to engage her audience on an emotional level.

she critiques many of her leftist allies for being bad at persuasion.

Socrates persuaded by both the logic of argument and the dynamic of fandom. Wynn is beginning to grow a dedicated following of her own: Members of online discussion groups refer to her as “mother” and “the queen,” produce fan art, and post photos of themselves dressed as characters from her videos.

she shares Socrates’s view that philosophy is more an erotic art than a martial one

As she puts it, she’s not trying to destroy the people she addresses, but seduce them

Wynn is a former Ph.D. student in philosophy, and though her videos are too rich with dick jokes for official settings, her argumentative practice would pass muster in any grad seminar.

One thing she has come across repeatedly is a disdain for the left’s perceived moral superiority. Anti-progressives of all stripes, Wynn told me, show an “intense defensiveness against being told what to do” and a “repulsion in response to moralizing.”

Matching her speech to the audience’s tastes presents a prickly rhetorical challenge. In an early video, Contra complains: “The problem is this medium. These goddamn savages demand a circus, and I intend to give them one, but behind the curtain, I really just want to have a conversation.

Philosophical conversation requires empathy and good-faith engagement. But the native tongue of political YouTube is ironic antagonism. It’s Wynn’s inimitable way of combining these two ingredients that gives ContraPoints its distinctive mouthfeel.

Wynn spends weeks in the online communities of her opponents—whether they’re climate skeptics or trans-exclusionary feminists—trying to understand what they believe and why they believe it. In Socrates’s words, she’s studying the souls of her audience.