Culture is a web of meaning-making patterns that consciously and sub-consciously guide, legitimize, and routinize human behaviors and perceptions evolving in a given communal context. The question under study for this essay is: what happens when different cultures interact with one another in a dynamic interplay of conflict resolution and national reconstruction in post-war societies? Analysis of the United Nations’ peace-building operations in Cambodia offers valuable insights into this inquiry. The case study will illustrate the turbulence of cultural confluence in which Cambodian Theravada Buddhism and Brahmanism interact with the distinct cultural tradition of Western democracy. The sustained tension that characterized the peace process in the 1990s is attributed in part to different meanings that the Cambodian factional leaders and the UN transitional authority attached to the sources of political legitimacy, the notion of time, and the significance of formal agreement, fairness, and neutrality. Western democratic norms and institutions introduced by the UN mission in Cambodia have encouraged pluralism, openness, and broad-based consensus building, while discouraging monopoly, closed-mindedness, and clique-based decision making. A closer look at the dynamics of the cultural confluence will reveal, however, that the UN-led democratization process, if not the notion of Western democracy per se, involves inherent tendencies to promote not only the former trends but also the latter. This dilemma of democratization generating non-democratic effects on the ground presents a paradox of democratic transition that both domestic and international policymakers must confront, in order to make peace processes more effective and sustainable.