In this article, Schellhammer's statements that learning is only possible in tension and that difference and diversity are prerequisites for tension are discussed in light of a certain event that occurred at a Summer School on Pluralism, Development, and Social Change. The article aims to explore Bildung, and especially learning in tension, through a concrete case study in which cultural diversity is a key issue. Reflecting on the case, psychological, philosophical, and sociopolitical perspectives are presented, each of which casts a different light on what happened. In the final reflection, we turn to the question of what dialogical self theory (DST) can offer when it comes to learning in tension, and how DST can be enriched and challenged by other approaches. We argue that DST facilitates the development of intercultural competence through dialogue with the unknown other in the self. Philosophical notions of cosmopolitanism and Socratic self-examination can shed further light on resistance to and conditions for transformative dialogues. They also place these in a historical and global perspective. We introduce an agonistic model of dialogue, in which the structural power inequalities and privileges people bring into dialogical spaces are explicitly addressed, thereby sowing the seeds of postdialogue transformative action in a personal and professional sense—for example, in transformative justice initiatives.