Interreligious dialogue does not take place in a vacuum, nor is it a matter of casual conversation. Dialogue is a contested phenomenon, advocated and embraced on one hand, eschewed and discarded on the other. By way of an exploration of the fact of plurality, the notions of modernism and postmodernism, and a brief discussion of select pertinent issues (unity, truth, and the very idea of theology), the paradigmatic context of pluralism will be critically discussed. Contemporary engagement in interreligious dialogue and interfaith relations requires to be underpinned by a carefully thought-out conceptualising of the context in which it can authentically occur. This paper seeks to contribute to the understanding of the context of and for interreligious dialogue.