This article begins by reviewing psychoanalysis's conflicted relationship with pleasure as both a desired and feared goal. Freud implicitly changed his stance on pleasure as he elaborated the meaning of his grandson's fort-da game suggesting that pleasure is necessary for the mastery of loss and trauma. This article discusses several current theoretical aspects of pleasure including a phobic attitude towards pleasure and the experience of confusion and doubt within the transference–countertransference relationship that occurs as a result of shared moments of pleasure. I suggest that shared experiences of pleasure are inherent aspect of change in psychotherapy because they allow externalized disowned aspect of the self to become internalized as active, meaningful subjective experiences. A lengthy clinical illustration is presented in which songs are used as pleasurable and frightening transitional experiences that allow for the expression and symbolization of disowned aspects of the patient's self.