This chapter investigates how an intentionally pluralistic Jewish high school in the United States called ‘Tikhon’ deals with questions regarding the individual and the community in its educational practice. It analyses what the practices reveal about its understanding of pluralism. The chapter argues that two dynamics are fundamental to Tikhon's efforts: first, the need to create an environment in which participants can risk the differentiation, debate, discussion, and openness to cooperation and change that are at the heart of Tikhon's understanding of community; and second, the need to create a psychological sense of community in which ‘difference’ is central to the conception of community. This chapter's enquiry is part of a larger project to study how pluralism is enacted and understood at Tikhon. It asserts that the approach and methods found at Tikhon can be applied to other settings where the tension between the individual and the group is central to the educational approach.