‘Woke Teen’ Dean Withers Debated 20 Trump Voters at Once. Now He Has a Message for Liberals

You might not recognize Dean Withers without Charlie Kirk sitting across from him. Or Nick Fuentes. Or 20 Trump supporters. Or any of the many conservative opponents the now 20-year-old college philosophy student went viral debating in the months leading up to the 2024 election. But now that the election is decided and exit polls show many of his fellow male Gen Z voters migrated to Trump, Withers stands apart not only from his opponents but also many of his peers.

Over the phone a few days after the election, Withers is the same sharp-witted and deeply informed person viewers saw in his breakout Jubilee YouTube video on September 8, when he was one of 25 liberal college students debating far-right political commentator Charlie Kirk. On September 20, he was brought back as the main character, facing off against 20 Trump supporters in another speed-debate that accrued 13 million views.

Withers’s TikTok following grew to over 2 million in the final weeks of the election, but he had been debating conservatives on livestreams and Twitter for some time. “The predominant reason I have these conversations isn't to convince the person that I'm talking to,” he tells GQ. “It's to convince people that are listening and that share the same beliefs as the person that I'm talking to.”

Withers was raised in a rural area of Colorado surrounded by conservative family members, and at first shared their beliefs—he has had to apologize for tweets he posted at that time that contained slurs. But he says it was conversations with those on the left, including his friends, and researching political issues more deeply that brought him to the conclusion that “typically the left is right.”

Withers has his work cut out for him. Here he shares his takeaways from the election results and what he thinks can be done about his generation of men skewing right.

Withers: It is accurate that younger men in my generation swing more to the right. On one hand, I'd say that the right has been winning the online culture war and non-legacy media avenues for a long time now. But we are just now seeing that [effort] prevailing more than ever before. One reason that we could attribute it to is [the mainstream media] highlighting points that society has seemingly neglected on a large scale. And a lot of these issues that are highlighted, because they need to be fixed and addressed, don't generally concern young men, especially young white men. When we're talking about these issues like systemic racism or BLM or the LGBTQ+ community or women's rights. What this can lead to is young men feeling as if they don't have any of that focus [on them], and sometimes this will lead these young men into spaces where they have that focus. And who is focusing on young white guys right now? The right.

Well, I mean, yes, of course, there's been instances where I've had conversations with people that have disagreed with me that have ended up shifting their beliefs to mine. But the predominant reason I have these conversations isn't to convince the person that I'm talking to, it's to convince people that are listening and that share the same beliefs as the person that I'm talking to. It's much harder to concede what you believe in when I'm preaching my beliefs in front of 20,000 people on a livestream. It's much easier to be scrolling on TikTok on your phone, on your lunch break, listening to a conversation or two of mine every day, and then over time, building up more of a foundational shift to the left because you start to realize that when you research the left is typically right.

Yeah. That has always been one of my focuses. But now more than ever, most definitely. I would absolutely say that seeing the fallout of this election, a main focus of mine is: How can we win the culture war? What attitudes have to be adopted to be more appealing to younger men in my generation, to have them hear me out?

Why progressivism upholds more of a focus on women, minority communities, LGBTQ+ communities instead of themselves. And typically the answer that they're met with from other people on the right is because [progressives are] lame, cringey, and weird. And more often than not when these young men go into the left, they're met with the answer that, well, you're just misogynistic and sexist. Adopt these ideals, or be isolated. And that is a very hard issue to solve. A lot of younger men that fall into these [right-wing] communities are misogynistic, are homophobic, are racist. So how do you open a space for dialogue to hopefully convince more of these younger men that maybe they're wrong?

Because I've shifted my focus in these individual conversations away from convincing the person I'm debating right now that they are wrong, and more so toward the promotion of social attitudes that I find beneficial to our country and humanity as a whole. And any role that I can play in what I see to be an inevitable progression toward what I believe to be more virtuous is my positive impact on the immediate world around me. And although these conversations can be hard, can be mentally draining, I inevitably see that greater purpose.

Yeah. I do. And on one hand, this is operating on the foundation that as society progresses, as we gain more efficient tools of the dissemination of information, uphold intellectualism to a higher degree, become more intelligent as a people, that we'll see more of a shift to the left because I find the virtues and beliefs of the left to be more grounded in reason and logic compared to those of the right. But maybe that's an assumption that is deserving of criticism, maybe it is the case that that won't be the outcome. But I ultimately believe that over the course of humanity, although there are a plethora of issues that are deserving of their own focus and to be recognized for the harm that they cause, one thing I could say is that seemingly over the course of humanity, things have gotten better. And that's on a very large, long-term, macro scale. So that is why I uphold the assumption that the more humanity progresses, the smarter we will be, the more rational will be, and more willing to adopt views found on the left.