This chapter discusses that some of the new and past efforts to understand play, and how these efforts are reflective of the way people think about reality. Play as unmasking is part of more general relation between play and anxiety. Safety is a prerequisite for play, and it is the safe confines of play that allow for the exploration of potentially threatening realities. Sigmund Freud’s theories of play were pushed into the realm of practice by psychoanalytic therapists who attempted to tailor psychoanalysis to children. The research on play has been conducted within a cultural context that views play as a frivolous diversion from the more important activities related to goal-directed behavior and work. Childhood fantasy play and children’s myths are developmentally idiosyncratic phenomenoa that disappear once the individual begins to develop these critical facilities. From an existential framework, play is the embodiment of the human capacity to wish; a capacity that is necessary for willing and responsible action.