This article performs a thought experiment. We ask: what if we were to engage two venerable legacies of dialectics, Hegelianism and Daoism, to see what results in terms of our thinking in International Relations (IR) about World Politics (WP)? Would some kind of a shift, synthesis, or transformation occur, as suggested by the dialectical goal of both traditions? Our discussion focuses broadly on the question of understanding social relations in world politics-the interconnectivity and complexity of social life and the potential for transformation it engenders-a question of increasing relevance for and in mainstream IR. We close by suggesting that aesthetics may offer a means for Hegelianism and Daoism to revitalize each other-a question to be pursued through further dialogue and research.