In this paper, I explore the problems of cultivating a critical attitude in pedagogy given problems with accounts grounded in critical social theory, rational liberalism and pragmatic esthetic theory. I offer instead an alternative account of criticism for education in open, pluralistic, liberal, democratic societies called 'pedagogy of difference' that is grounded in the diversity liberalism of Isaiah Berlin and the dialogical philosophy of Martin Buber. In our current condition in which there is no agreement as to the proper criteria for assessing attitudes and actions, for a critical attitude to gain a foothold one must learn to evaluate proposed beliefs and behaviour-based standards within a particular tradition as well as those drawn from another viewpoint. To know oneself, one must engage others who are different. But to engage others in a meaningful way one must be immersed in a tradition to which one is heir or with which one chooses to affiliate.