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In this article, we discuss the technique of the Squiggle Game (SG) and aim to shed new light on it by illustrating it with a clinical vignette. We present the case of a depressed adolescent for whom the use of SG as a wildcard avoids traumatic repetition and allows the creation of a therapeutic space that contains the paradox of guaranteed safety and the use of the unexpected. We begin by recalling the SG technique invented by Winnicott and then our own use of this technique. We then describe the clinical situation of a young depressed adolescent. We then discuss the therapeutic effects observed, linking them to the recognition of the need for security. We describe how the SG joker reduces patient– therapist asymmetry, helps to moderate interpretation and encourages a side-by-side situation. In the case of adolescents, their narcissistic fragility makes psychotherapeutic approaches difficult, so long-term SG offers a technical way of taking account of the need for security that this fragility entails. We depart from Winnicott by offering the SG technique over a long period of therapy, and we make theoretical and clinical suggestions based on our original use of SG.