This article evolved from a group process where members of a psychoanalytic institute were faced with planning workshops for a professional weekend around the theme of “play.” The workshop that evolved consisted of four vignettes of play taking place in the therapeutic sessions of a child, an adolescent, an adult, and an elderly woman. The discussion of these vignettes that began at the conference and then was developed for this article focuses on tracing the development of play from childhood into adulthood (Mayes & Cohen, 1996; Russ, 2004) and on the relationship between play and the development of reflective functioning (Fonagy & Target, 1996). One area of particular interest that was focused upon was the use of play with adults who are described as “concrete,” people who function, at times, at a level of differentiation more typical of a young child. Play is described as being particularly helpful in facilitating a more differentiated and, thus, more reflective mode of psychic functioning for this group of individuals as well as for people at all levels of development.