In his book The Argumentative Indian, Amartya Sen has brought attention to India’s long tradition of accommodating diversity through public discourse and debate. This toleration of diversity, according to Sen, has been ‘explicitly defended by strong arguments in favour of the richness of variation, including fulsome praise of the need to interact with each other, in mutual respect, through dialogue’.2 In this chapter I would like to explore Sen’s claim by focusing on three dialogues from traditional sources: the Ajātaśatru-Gārgya dialogue in the Bṛhadāraṇyaka Upaniṣad, the Soṇadaṇḍa Sutta of the Dīgha Nikāya, and the Janaka-Sulabhā dialogue in the Mahābhārata. First, I will bring attention to how each dialogue depicts an encounter between disputants who are defined by their differences, whether these differences are along the lines of caste, religious tradition, or gender. Then, I will explore how each dialogue confronts the differences between the two characters and their viewpoints both by offering a perspective that transcends the differences between the characters and by leaving the outcome of the debate to some extent open-ended, thereby accommodating both perspectives. As we consider each dialogue within its larger textual context, I will suggest that these encounters with difference can be seen as a crucial and recurring aspect of Indian religious and philosophical literature. These three dialogues, along with many of the other dialogues considered in this book – particularly those discussed by Geen and Nichols – have interesting implications regarding current attempts, by Amartya Sen and others, to recover an ancient Indian tradition of argumentation and toleration.