This chapter shows that Donald W. Winnicott's notion of playing with reality as a model for conceptualising the manner in which the subject can succeed in representing and knowing his emotional states in the encounter with reality. Enactment becomes the symbol that represents and communicates the unconscious emotion which links the members of the analytic pair. In other words, it allows an unconscious emotional state to be rendered conscious by making it perceptible in the form of drama and, hence, susceptible to narration in words created by the ego. This chapter also shows that Sigmund Freud's notion of Agieren be rendered in English by enactment rather than acting out. When the events occur in the analytic process, they are called enactments owing to the involvement of both the transference and the countertransference. The chapter demonstrates the power and inertia of playing within the processes of both analysis and supervision.