In this article I review some of the ways in which the themes of authenticity, spontaneity and improvisation have become important values in the writing of many contemporary psychoanalysts. I examine the emergence of this trend in the context of historical and cultural changes in the construction of the self, and the fragmentation of traditional beliefs and social structures linking the individual to the collective. I also explore the relationship between the principle of authenticity and various dimensions including autonomy, mutuality, intersubjectivity, and the ethical realm. In addition I explore the perceived tensions between traditional social forms and the experience of authenticity, and examine the implications of the questions raised in this essay for our conception of the nature of psychoanalytic practice.