This paper explores the issue of individuals in Confucian tradition from a comparative perspective, by viewing it alongside of American Pragmatism, as expressed by the philosopher John Dewey. Dewey devoted much effort to describing people as necessarily social beings without losing track of their status as unique and independent individuals capable of forming the basis of a democratic society. It is striking to note the converging points in the two remote strains of thought on the relationship between an individual and a society. By taking a comparative perspective, my aim is to describe the points where the two diverge in their views on the relation between individuals and society, and to examine how their notion of the individual can lead all the way to an uncompromising insistence upon democracy in the case of Dewey, but fail to envision democracy, and even still impeded efforts to bring it about in a full-blown sense in the other. Confucianism, I argue, suffers from inner conflicts that pose a particularly important contemporary dilemma, and has to meet a challenge of making itself compatible with democratic ideals of equality and individual freedom. Dewey’s thoughts on the relation between the individual and the society could help us reinterpret Confucian ideas of individuals.