If you bring Swedish and South African undergraduate students together in a semester’s joint study of Human Rights and Democracy – can they understand one another? Will they through the learning processes get more perspectives to the knowledge they had beforehand e.g. concerning their own country and its contemporary challenges? Or to phrase the question just slightly different, can a group of South African and Swedish researchers discussing Human Rights and Democracy understand one another? Or are their background experiences from their respective societies informing their research and theories so different, so as to make understanding impossible? Experiences like these form the background to the issues of diversity and epistemology discussed in the chapter. Initially different understandings of diversity are reviewed. Further, challenges stemming from more of diversity in multicultural societies are addressed in relation to theories of citizenship. A central focus in the chapter is on epistemological issues. A positivistic understanding of epistemology is critiqued and replaced by another one taking the subjectivity and “situatedness” of knowers into account. As a consequence truth claims, dialogue and value relativism are addressed. After a discussion of the praxis of Gandhi the chapter ends in an argument for the need of questions of knowledge, truth and dialogue to be dealt with by educators, this for them to adequately grapple with the contemporary complex challenges. Theories by Seyla Benhabib, Iris M Young, Donna Haraway and not the least Lorraine Code are interpreted and used in the argument spelled out by the author.