This episode explores the potential of AI in intimate and consequential conversations, particularly within family life, featuring Kelly Corrigan's conversation with Dr. Alison Darcy, the creator of Woebot, an AI therapy tool. Against the backdrop of increasing mental health needs and limited access to traditional therapy, Darcy developed Woebot to provide support anytime, anywhere, emphasizing that it meets people where they're at, especially during difficult moments. Corrigan initially skeptical, questioned the role of AI in emotional interactions, but Darcy clarified that Woebot is designed to be a tool for self-improvement, not a replacement for human connection, and that it is based on cognitive behavioral therapy and is scripted rather than generative. More significantly, the discussion pivoted to the ethical considerations of AI therapy, including concerns about privacy, control, and the potential for creating dependency, with Darcy highlighting Woebot's commitment to user well-being and its business model, which is based on partnerships with health systems and not on maximizing engagement for profit. The conversation concludes with insights on how AI can model healthy interactions and provide accountability, potentially improving communication in real-life relationships, and emerging industry patterns reflected in the need for smarter evaluation of AI options to ensure they serve human betterment.