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When behavior is reported that objectively places the patient and others at risk and subjectively exposes the therapist to a vivid range of private experience, the challenge in maintaining a clinical stance is complicated to say the least. This complication is intensified to the degree that the clinician's aim involves understanding rather than discipline and control. To specify details of that challenge, I discuss two patients whose unsafe sexual practice confronted me. In these clinical situations, I found it useful to be mindful that bareback sex contains a range of meanings, including the search for a quality of relating that can enliven an inner deadness. Thinking this, I found it necessary to be alert to wishes for creativity as well as destructiveness. Attending to such paradoxes also required me to come up with a new way of working with countertransference: to render it an imaginary theatrical performance.