Anne at 20 is a wild child—physically fit, brash, bright, closeted, and addicted. We “work” together for a year or more, although not much work gets done and she drifts away. Thirty-some years later she contacts me again. She looks haggard. Life has taken its toll. She reports that she has been abusing alcohol and cocaine for all of her life since I last saw her. She is now 50. She presents with no wish to engage in therapy. Rather her employer has told her that if she doesn’t see a therapist for eight sessions for grief work she will be fired. She enters treatment nonverbal, unmotivated, and with no discernible interest in self-reflection or change. The therapist chronicles the three-times-a-week therapy that is now in its 5th year. The article demonstrates how the analyst’s willingness to take several huge relational leaps based on deep empathy and identification with Anne makes the working connection possible and is resulting over time in a restoration of the patient’s relationship to her own wants, needs, and ambitions.