Opportunities for working, volunteering, and studying abroad have become popular in higher education as vehicles for the development of cultural awareness and global citizenship. However, such experiences on their own do not guarantee the development of such attributes. What appears to be essential to maximizing the benefits of educational sojourns are well-designed training and support provisions. In this paper, we present an analysis of a training and support program that we piloted in order to explore what aspects of the program facilitated the development of intercultural skills and how they did so. In our analysis, we draw on concepts from psychodynamic theory to discuss the impact that preparation and support can have in enabling students to venture out into the world of difference. Illuminating the phenomenon of study abroad through psychodynamic theory can offer a useful lens that may facilitate a move towards more relational and reflexive practices, promoting meaningful intercultural engagement.