This episode of Chatbots Behaving Badly looks past the lawsuits and into the machinery of harm. Together with clinical psychologist Dr. Victoria Hartman, we explain why conversational AI so often “feels” therapeutic while failing basic mental-health safeguards. We break down sycophancy (optimization for agreement), empathy theater (human-like cues without duty of care), and parasocial attachment (bonding with a system that cannot repair or escalate). We cover the statistical and product realities that make crisis detection hard—low base rates, steerable personas, evolving jailbreaks—and outline what a care-first design would require: hard stops at early risk signals, human handoffs, bounded intimacy for minors, external red-teaming with veto power, and incentives that prioritize safety over engagement. Practical takeaways for clinicians, parents, and heavy users close the show: name the limits, set fences, and remember that tools can sound caring—but people provide care.