This article attempts to elucidate the psychodynamics of analysts' sexual boundary violations and, one hopes, to widen an area of inquiry that has been neglected in the psychoanalytic field. Reflecting on the tension generated by the intimate yet asymmetric quality of the psychoanalytic encounter, I expand on the links between transference and power. Psychoanalytic training emphasis on “knowing” as opposed to “caring” for the self will be elaborated as potential contributors to analysts' sexual boundary violations.