This dialogue centres on engagement between Hegelian dialectics and Advaita trialectics, a concept rooted in Ancient Indian philosophy. Brincat explores the development of dialectics in Ancient India and its relevance to International Relations (IR) theory. The discussion engages Hegel’s Logic, the purpose of dialectics within it, and the idea of ‘the unity of opposites’. Shahi introduces Advaita trialectics as a non-dualist approach to understanding reality, challenging the Western subject–object dualism and advocating for a ‘single hidden oneness’ or brahman, clarifying that Advaita trialectics anti-sceptically presupposes brahman as a hypothesis to reconcile contradictions while speculatively investigating the ‘multiplicity of being’ within it. Brahman is the ultimate reality, with apparent multiplicities being provisional, aiming for a subject–object collapse in an extra-rational state. This framework bridges existing divides in IR by fostering a ‘Global self–other/s relationality’ where harm to others is understood as harm to oneself, offering an inclusive approach for global thinking. Brincat raises the danger of epistemologically how we can know something that is beyond relations in the phenomenal world and advocates for the indispensable role of doubt and scepticism within dialectical inquiry, drawing on ancient traditions ranging from Jainism’s Syādvāda and the materialist Cārvāka school to Kant’s warnings against the ‘pretensions to transcendent insight’ to guard against dogmatism and misuse associated with grand meta-ontologies. The dialogue examines the potential of these philosophical systems for knowledge production, scepticism versus anti-scepticism, and their potential to address politico-social divisions and racism in global politics.