The aim of this paper is the exploration of Kegan’s constructive-developmental theory through the analysis of the behavior of an agent within Wenders’s film Alice in the Cities, which is used as a case study. In the first part, we will approach Kegan’s ideas regarding the evolution of human beings’ consciousness as they move through five progressively more complex orders of consciousness. We will also approach the connections of Kegan’s perspective to Mezirow’s Transformation Theory. Then, we will draw insights from the film in order to expand the exploration of some crucial issues of Kegan’s theory, such as: How is a person’s consciousness developed? Are there signs, when a person is situated in a certain order of consciousness, that he/she has the potential to move toward a next one? Which might be the adult educator’s role in assisting the learners’ evolutionary process? Finally, in the last section, some limitations of Kegan’s perspective will be critically discussed. (DIPF/Orig.