This paper presents the first results from a longitudinal qualitative study following 38 Danish students' choice of higher education. By using a narrative psychological framework it is shown how the choice of higher education is embedded in various dilemmas, making it difficult for the students to make meaningful choices. They believe the choice should be unique and individual and that it should correspond with who they are and wish to become. However, the analysis shows that choosing what to study after upper-secondary school is a complex ongoing and social process, rather than an isolated individual event. Implications of these results are discussed and the educational system is urged to provide room for and facilitate students' production of choice narratives.