New York Times technology columnist and host of the Hard Fork podcast Kevin Roose (@kevinroose) joins Andy, Jesse and Matt to talk about his infamous, amorous encounter with Bing Chat/Sydney, Sydney's response to his story, getting backhanded compliments from John Oliver, how ChatGPT was dismissed by its own creators, generative AI and the future of deepfakes, AI's capability overhang, explaining LLMs' weirdness with the Waluigi effect, artists' lawsuits over training AI on their creations, whether we care how art is made, which jobs could soon be on the chopping block and Futureproof, Kevin's handbook for the weird times ahead.