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I have written previously about the allure and hazards of that “promise of love” that can be a siren’s call luring us into terrible dangers (Charles, 1999). The intense intimacy of the analytic environment is also regressive, pulling on primitive memories that have a heightened, sensory quality, often having to do with early experiences of frustrated desire. Psychoanalytic psychotherapy invites the patient to transfer feelings from childhood and later life onto the analyst. Coming into contact with primitive and forbidden longings helps the individual make sense of forces that drive her thinking and action. For such powerful forces to be unleashed, the consulting room must be a place of safety in which fantasies can be enacted without fear of actualizing them. The analyst, too, feels these regressive desires but must be able to stand her ground and allow the transference to unfold such that the patient can encounter her longings and desire and work her way through them rather than expecting them to be filled in the consulting room. Two cases are described in which such boundaries had been broken and the patients sought assistance in dealing with the sequelae. These cases remind us that our own desires to be the perfect parent or analyst can be obstructive and destructive if we lose our analytic mind and move into the realm of transgressive enactment rather than preserving the space for working through.