In my response to Guzzardi’s paper, I trouble the notion of gender play by arguing that it must be contextualized in order to be comprehended and fruitfully used for therapeutic purposes. It goes without saying that a certain amount of safety is required for play to be possible. In my paper, I inquire into the nature of the safety necessary for gendered play. I argue that embedding the patient, the therapist, and the dyad in context, history, and sociopolitical conditions is a fundamental component of said safety, that without this embedding, gender play is not only not possible, it is itself unsafe. Finally, I offer a way for clinicians to engage in this process of embedding through the notion of the systemic enactment, which opens a path for healing that surpasses the individual and extends out into the community, the very space in which we are all embedded together. This embedding represents the sort of safety needed for gendered play to be generative and enlivening, and for therapy to be liberatory.