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People with pathological narcisism, with their conflicted sense of grandiosity and vulnerability, often pose a variety of therapeutic challenges, which may impede these patients’ ability to benefit from psychotherapy. To offer a case illustration and provide insight into the intrinsic difficulties of working with this patient group, we examined the treatment of a fictional character, Alex, from the TV series In Treatment. Based on the Shedler-Westen Assessment Procedure-200 we diagnosed Alex with pathological narcissism, and evaluated the treatment process (seven sessions) by reporting on measurements of session-by-session change in explicit working alliance, implicit language alliance, and ruptures and repairs. Over the course of treatment, the working alliance (Working Alliance Inventory-Observer scale) fluctuated with a particularly low bond at session five, identified as a rupture (Rupture Resolution Rating System). Language analysis (Linguistic Inquiry and Word Count) showed that the unconscious aspects of the alliance started to deteriorate just before the rupture occurred. The results illustrate how therapists might be pulled to collude with narcissistic patients’ grandiosity, with the risk of neglecting their vulnerability. This fictional portrayal of a treatment with a narcissistic patient may be widely shared with researchers, students and therapists alike, offering a common locus of scholarly attention, and an innovative tool for teaching. Given the lack of empirical treatments for pathological narcissism and the great therapeutic challenges narcissistic patients present, further research and development of clinical guidelines are warranted.