In this article, we explore the practice, promise, and contradictions of introducing liberatory practice into a higher education classroom. Freire introduced liberatory education in response to the hierarchical transfer of knowledge, “banking” concept of education that has dominated educational institutions. The banking approach to education demands that students memorize and repeat top-down “official” knowledge in order to achieve success. Liberatory pedagogy holds great hope, but developing a space for liberatory dialogue within the university classroom remains messy and rife with contradictions. Professors interested in liberatory pedagogy must make explicit the contradictions and challenge the multiple ways schools shape students, politically and culturally. We reflect on three different points in the semester as moments of explicit focus on the contradictions of creating liberatory spaces and dialogue within higher education. Location matters in every moment: our social locations shape our experiences, and the location of the classroom within higher education and the shifting locations in the liberatory process include managing the contradictions and possibilities of human liberation. We offer educators wishing to develop liberatory practices some ways of reflecting on and shaping a liberatory space within higher education classrooms through the lens of a professor and student engaged in the process of liberatory dialogue.