In this chapter, we investigate imagination in children’s pretend play in a cultural life course perspective. This perspective underlines the relation between play and the cultivated and personalized life of the players. It points to the processes in which meaning making takes place through play: imaginative playing transcends the immediate context of the play and feeds back to the player as engaged an being-in-the-world with others, contributing to the directionality of the cultural life course on social as well as personal levels. Whereas play is generally recognized as an important developmental vehicle of children, it tends to connote a childish or immature behavior when applied to adult behavior and is often replaced with terms such as “creativity.” We will investigate this relation, partly as a scientific and societal discourse of what it means to be a child or an adult, and partly as a developmental process of imagination.