Character.AI is where Shakespeare meets Snapchat and your anime boyfriend quotes Nietzsche in real time. In this episode, Emily Laird explores the company turning chatbot conversations into Gen Z’s favorite form of weird therapy and role-play. Founded by two ex-Googlers (Transformer royalty, no less), Character.AI has raised big money, signed a $2.7B deal with Google, and racked up millions of users—most of them teenagers asking emotionally complex questions to digital raccoons. But with rising scrutiny, spicy scandals, and a moderation system held together by bubblegum and vibes, can Character.AI survive the AI drama it helped create?

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