Three characteristic transference configurations are identified that frequently emerge in the analyses of patients for whom deception and inauthenticity are central themes. These configurations are labeled (1) imposturous, (2) psychopathic-paranoid, and (3) psychopathic-unreal. Patients who develop these transferences have actively split the object world along two distinct axes. The first split has occurred along the lines of pleasure and unpleasure. The second divides objects along the lines of the experience of reality, with some objects felt to be charged with exaggerated, painful meaning, and others felt to be devoid of meaning and affect. This split, which arises as a way of managing painful object relations, is then woven into fantasy and defense at many developmental levels. Material from the analyses of two patients is presented to demonstrate the interplay of the three transference configurations, the fantasies that underlie them, and the clinical importance of analyzing the second split.