Spontaneity—a dimension of the subjective experience of the individual and improvisation—the rules of engagement as established in the theater arts, are described as intrinsic to the analytic dialogue and as frequently facilitating the therapeutic process. After a review of the relevant contemporary psychoanalytic literature, clinical material is presented to illustrate the psychoanalytic value of improvisation in opening up new areas of exploration and new modes of participation. The various theoretical formulations of the clinical example are discussed to support the proposition that spontaneity and improvisation are essential to all psychoanalytic conversations.