Adam talks with Natalie Wynn, ContraPoints, about the challenges of being a YouTube creator, the weirdness of time spent online, Gamergate, and the dark side of the internet. They discuss navigating delicate topics in video essays and the importance of dignity. They also share their love for dreamy ambient music and recommend the album 'Pearl' by Harold Budd and Brian Eno.

Natalie Wynn, known as Contrapoints, helps us understand LGBT conservatives and the division within queer political groups. They discuss the emergence of conservative queer influencers and the reasons behind their views on non-binary people. The conversation explores the use of euphemism in politics, delves into the struggles of gay conservatives, and navigates the complexities of differing beliefs within a friendship.

Natalie Wynn, YouTuber behind ContraPoints, discusses gender, conspiracy, and academia’s role in the digital age with Adam Conover. Topics include exploring sexuality through Twilight, controversial themes in the series, connections between philosophy, comedy, and sexuality, gender roles, academic background, content creation challenges on YouTube, protecting personal information, and the value of creativity in media content creation.

Natalie Wynn, known for her captivating video essays as Contrapoints, shares her insights on navigating today's complexities. She discusses the interplay of dread and hope in political landscapes, especially for marginalized communities. Wynn tackles childhood fears surrounding climate change, emphasizing resilience and the power of nurturing hope. She also reflects on the challenges of building genuine connections in the LGBT community, contrasting online interactions with real-life relationships. Through it all, her artistic approach highlights empathy and personal growth.

Natalie Wynn, known as ContraPoints, explains how she de-radicalizes viewers with right wing politics. They discuss the internet's turn towards fascism in 2017, incentivizing reactionary beliefs, the power of persuasion, balancing seriousness and joy in politics, and cancel culture's impact on personal growth.