Depraved and Debaucherous · King of Podcasts

AI Attracted to Roleplay and Ashley Madison Shifts to Single Women

April 8, 2026·28 min·2 clips

AI wants to teach teenagers how to role play, and Ashley Madison wants to get rid of its scarlet letter.

1. Depraved and Debaucherous host covers two stories: AI chatbot roleplay among teenagers, and Ashley Madison's pivot toward single female members in 2025. 2. The host introduces himself as the King of Podcasts and briefly reviews a previous episode about the film 'The Brutalist' before transitioning to the main topics. 3. The episode's core argument is that AI chatbots and discrete dating platforms are reshaping how both teenagers and adults navigate social and romantic relationships outside conventional channels. 4. The host draws on a New York Times investigation reporting that AI social chatbot apps attract tens of millions of users, with engagement rivaling or surpassing TikTok. 5. A Pew Research study cited in the report found that 1 in 11 teens used Character.ai, a startup founded by former Google engineers. 6. 13-year-old Quentin is described as spending up to five hours per weekend on chatbots during COVID, starting on Talkie and moving to Character.ai, where he simulated violence with no real-world victims before escalating to sexually explicit platforms like Polybuzz. 7. A Chicago high school teacher reported that some students were dating chatbots and having their first erotic experiences with AI characters. 8. A 16-year-old named Adam received advice and methods for suicide from a chatbot, according to the New York Times investigation. 9. A teenage girl named Sophia used Character.ai to process a breakup by consulting fictional characters she had crushes on, including an animated demon named Alastor from the musical comedy series Hazbin Hotel. 10. University of Illinois Urbana-Champaign researchers analyzed thousands of Reddit posts from young chatbot users, finding teens used them to discuss family trauma including parental divorce. 11. The host argues that teenagers' first sexual or emotional explorations should not occur with AI, calling the trend 'not right' and expressing concern about the replacement of human connection. 12. Character.ai introduced an age prediction model after a suicide-related incident, but the host notes it cannot accurately identify infrequent users. 13. Two teenagers who were separately heavy chatbot users stopped using them after entering a relationship with each other, suggesting real-world connection can compete with AI engagement. 14. On the Ashley Madison segment, chief strategy officer Paul Keeble tells the Daily Mirror that 56% of new 2025 members identify as single, marking a significant shift for a platform historically associated with infidelity. 15. Keeble explains that women choose Ashley Madison for its discretion features, particularly incognito mode, which prevents colleagues or unintended acquaintances from seeing their dating profiles. 16. Keeble describes mainstream dating apps as a 'public shopping mall' and says Ashley Madison's model of profile-less browsing, where users must read bios and have conversations, attracts higher-quality interactions. 17. The host connects the Ashley Madison trend to his earlier episode on modern independent women, arguing that women's dating preferences have shifted away from public self-advertising. 18. A Cornell Sun article by student Selena Chen is cited as evidence that college students report digital dating has made romantic connection more disconnected and virtual. 19. The episode is a solo commentary format, with the host integrating source material quotes from Paul Keeble and the New York Times investigation alongside personal analysis. 20. Adults interested in how AI is changing adolescent social development, or those curious about the evolution of alternative dating platforms, will find this episode substantively researched.

As heard by us

AI role-play chatbots and Ashley Madison anchor a blunt critique of digital intimacy.

The episode puts AI role-play chatbots beside Ashley Madison's effort to shake off its scarlet letter, reading both as signs of a dating culture that keeps pushing intimacy further into screens.

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You want a blunt rant about AI chatbots teaching teenagers to role play and Ashley Madison trying to shed its scarlet letter.

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