As we attempt to engender a dialogue between different philosophical traditions, one of the first – if not indeed the first – of the topics which need to be addressed is that of the very nature of dialogue. In other words, we need to engage in a dialogue about dialogue. Toward that end, this essay attempts to rethink the nature of dialogue from the perspective of two key members of the Kyoto School, namely its founder, Nishida Kitarō (1870–1945), and its current central figure, Ueda Shizuteru (b. 1926). The Kyoto School is the most prominent group of modern Japanese philosophers, whose thought emerges from the encounter between Western and Eastern traditions. This essay seeks to elucidate and further unfold the implications of rethinking of the nature of dialogue from the perspective of Nishida's and Ueda's primarily Zen Buddhist reception of and response to Western philosophy.