This article addresses several conceptual ambiguities, contradictions, and vagaries that can play a part as either an unconscious backdrop or as a conscious rationale for sexual boundary transgressions. The first revolves around the nature of transference, in particular, its real or unreal character. Second is a question of whether the violating analyst ever truly loved the patient, a question with which the victim-patient can wrestle for years in the aftermath. Third, the essential function and nature of boundaries is addressed as a process that is continually renegotiated along the axis of self-other differentiation. Finally, the fundamental dynamic of the relationship is taken up with the question, who were the patient and analyst to each other? The theoretical assumption of multiplicity belies this unidimensional query and reveals a collapse of complexity in the analytic temporal and spatial expanse. It is hoped that the clarification of these fundamental concepts will at least give a moment’s pause before the slide down that destructive slope. In addition, for those of us treating victims and/or analysts who have transgressed, these theoretical clarifications will help guide our work in resolving the many conundrums associated with the aftermath of this persistent and continually vexing problem.