Within dramatherapy and psychodrama, the term ‘de-roling’ indicates a set of activities that assist the subjects of therapy in ‘disrobing’ themselves from their fictional characters. Starting from the psychological needs and the therapeutic goals that ‘de-roling’ techniques address in dramatherapy and psychodrama, this text provides a broader understanding of procedures and exercises that define and ease transitional experiences across cultural practices such as religious rituals and spatial design. After this introductory section, we propose a tentative answer as to why game (...) studies and virtual world research largely ignored processes of ‘roling’ and ‘de-roling’ that separate the lived experience of role-play from our everyday sense of the self. The concluding sections argue that de-roling techniques are likely to become more relevant, both academically and in terms of their practical applications, with the growing diffusion of virtual technologies in social practices. The relationships we can establish with ourselves and with our surroundings in digital virtual worlds are, we argue, only partially comparable with similar occurrences in pre-digital practices of subjectification. We propose a perspective according to which the accessibility and immersive phenomenological richness of virtual reality technologies are likely to exacerbate the potentially dissociative effects of virtual reality applications. This text constitutes an initial step towards framing specific socio-technical concerns and starting a timely conversation that binds together dramatherapy, psychodrama, game studies, and the design of digital virtual worlds. (shrink)