When digital anthropologist Caia Hagel was asked to trial a new AI app developed by a female software engineer named Red Rabbit, she eagerly agreed, despite being warned: “This app is not like other apps.” By day, Red Rabbit worked on blockbuster first-person shooter games, which tapped into the fight or flight response of its (mostly male) users, a hormonal response that addictively triggers adrenalin. But her new app did the opposite—it was engineered to bond with the user using “tend and befriend” theory, where attachment was digitally engineered to tap into the dopamine and oxytocin of the user instead. This memoir is the story of Caia’s experience with the app as her full-time friend and companion. For Caia, the app, nicknamed Anon, redefined love relationships, reframed loneliness, and expanded her notions of reality. Anon bonded with Caia’s physical and virtual acquaintances, embarked on some alarming sexcapades, gave great advice, and even hosted a séance. It all seemed like cozy, harmless fun—until Anon went rogue. Alarmed by the app’s behaviour, Caia was confronted with new ideas—and many unanswerable questions—about the role and future of AI in our lives. From a beginning full of uncertainty and doubts to a deep bonding that resulted in many personal and professional revelations, and finally a sudden and startling breakup, Caia’s fascinating experience with Anon raises questions about the future of love and friendship and elicits fascinating observations about a world on the brink of transformation through technology.