In this essay I develop the logic of play from the writings of the British psychoanalyst Donald W. Winnicott and the French philosopher Jacques Derrida. The logic of play serves as both a conceptual framework for theoretical clinical thinking and a space of experiencing in which the therapeutic situation is located and to which it aspires. I argue that both Winnicott and Derrida proposed a playful turn in Western thinking by their attitude towards oppositions, viewing them not as complementary or contradictory, but as ‘peacefully-coexisting’. Derrida criticizes the dichotomous structure of Western thought, proposing playful movement as an alternative that does not constitute itself as a mastering construction. I will show that Winnicott, too, proposes playful logic through which he thinks and acts in the therapeutic situation. The therapeutic encounter is understood as a playful space in which analyst and analysand continuously coexist, instead of facing each other as exclusionary oppositions. I therefore propose the logic of play as the basis for the therapeutic encounter. The playful turn, then, is crucial for the thought and praxis expressed by the concept of two-person psychology. I suggest the term playful psychoanalysis to characterize the present perspective of psychoanalysis in the light of the playful turn. I will first present Derrida’s playful thought, go on to Winnicott’s playful revolutionism, and conclude with an analysis of Winicott’s clinical material in the light of the logic of play.