This article asks why adults play dress-up and investigates the role of object play in the making of magical thinking and the reforming of adult identity. The author looks at a wide spectrum of narratives and their genres--the fairy tale "Cinderella," the film comedy "Some Like it Hot", the epistolary novel "Pamela", the film melodrama "Now, Voyager", the psychoanalytical case study of "Miss K.," and the memoir "My Judy Garland Life". She asserts that these narratives help define what constitutes "a woman's story" as a story of transformation by setting its representation in relation to objects or aesthetic worlds, into which the woman changes or immerses herself with the same intensity and single-mindedness as a child at play. The author draws on the works of psychoanalyst Christopher Bollas to explain the transformational object seeking and aesthetic moment of these narrative representations and argues they model a woman's longing for transformation and make it imaginable to the adult mind. (Contains 2 figures.)