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How can we understand moments when the analyst lies to her patient? When it’s not the patient’s lying at issue but the analyst’s? When we suddenly find ourselves being deliberately disingenuous in the analytic hour? When our commitment to authenticity conflicts with the patient's need to create and sustain certain fantasies about us? Psychoanalytic literature typically focuses on the dynamics of the patient’s lie but rarely is the analyst's authenticity questioned. Are there times when the analyst might choose to lie in order to preserve herself, as well as, the relational bond? The complexity of this “choice” is explored and the erosion of an analyst’s authenticity unpacked during the final days of a difficult treatment.