Through three detailed clinical vignettes, the author explores the ethical undergirding of play. He defines play as a form of idiomatic responsiveness that emerges in the context of analytic intersubjectivity, one that can illuminate elements of fixed transference-countertransference enactment. The author outlines an ethic of play that considers whether the analyst’s forms of responsiveness deepen and enliven the patient’s understanding of unconscious fantasy, conflict, and internalized object relations. Play poses challenges and a potential risk for the analytic couple, since in play rules are often changing in the dialogue between the conscious and unconscious minds of the analytic couple.