In his book, “Playing and Reality,” Winnicott discusses a female patient whose way of coping with loss is interpreted as involving an attachment to the void. Referring to Benjamin’s and Alvarez’s works, I propose that Winnicott is describing an early stage of therapy in which the analyst struggles to separate himself from the patient’s sense of abandonment, and is unable to fully manage the sense of loss. This obstacle appears to have been caused by the intensity of the patient’s rejection, which was yet to be fully processed in the analysis. I argue that to overcome such difficulties, it is necessary for the analyst to confront their unconscious desire to be validated by the patient as a source of aliveness. I illustrate this idea using a clinical case involving a six-year-old child. In time, Winnicott achieved this separation, as described in the paper, “Fear of Breakdown” (1974), in which a patient’s “no one from nowhere” state of existence is understood intersubjectively.