In the course of an analysis, the analytic relationship can go through moments of difficulty generated by patient and analyst while they learn to “play” together. In this paper, different kinds of difficult relational moments are illustrated through fragments of a child analysis, and some components are explored that can catalyze the creative transformation of turbulence and the resumption of analytic “play.” In particular, the author hypothesizes that some conscious feelings described by Winnicott as characterizing play, understood as the optimal functioning of the analytic process, can be indicators of the efficiency of—or, conversely, of difficulties in—the unconscious oneiric work carried out by the couple. These indicators may be useful in monitoring the process not so much in the immediate moment, but rather over a medium to long period. Considering these indicators can initiate the revival of a playful equilibrium in the bi-personal system on which play and the analytic field are based.