Focusing on a lived and practiced tolerance, this thesis sets out to explore questions concerning education for tolerance, and, specifically, how teachers and educators can prepare students to become tolerating subjects in their everyday encounters with others. Taking its point of departure in real and fictional classroom situations, the overall purpose of the study is to explore the ethical and transformative potential inherent in education for tolerance. The theoretical frame of the study is deconstruction and the philosophical writings of Jacques Derrida. The purpose of the thesis is accomplished in three movements. The first aims to show why teachers and educators need to redirect their attention in the classroom if the ethical and transformative potential that lies in education for tolerance is to be taken seriously. Instead of focusing on the tolerated and “deviating” other, it proposes that the tolerating subject should be the center of attention. The second movement aims to prepare the ground for a deconstructive reading by mapping different contemporary discourses of tolerance. Three distinct but interrelated dilemmas of tolerance are identified: the dilemma of welcoming, the dilemma of drawing boundaries, and the dilemma of bearing or enduring the otherness of the other. The third movement aims to show how a deconstructive reading of the dilemmas of tolerance can help teachers and educators to perceive and relate otherwise to the tolerating subject in education. For this, I turn to Derrida’s deconstructions of three concepts that are vital for our understanding of tolerance: hospitality, justice and mourning. The final section of the thesis discusses some educational implications deriving from the study. It is argued that if we look at the tolerating subject through the experience of its deconstruction, we also come to see education for tolerance otherwise. What this altered perspective can mean for education is articulated within the framework of what is called a pedagogy of tolerance.