Discussing an intensive case study of female sexual dysfunction, this paper studies mutual deregulation and disintegration as it unfolds in the transference-countertransference dyad. I propose that ethical transgressions are potentiated in analytic dyads in which the analyst's hope for either solitude or mutuality is foreclosed. This hope can be foreclosed by the particulars of the therapeutic interaction as well as by the theoretical and clinical aspects of analytic training. The deregulation that both precipitates and follows such transgression can be healed (in the analyst, in the analysis) only by the restitution of the therapist's agency, the reduction of paranoid-schizoid guilt and shame, and the location (in the analyst) of depressive, “I-Thou” remorse.