The article discusses recent historiographical approaches to the question of Jewish conversion to Christianity in Europe in the Middle Ages. It outlines the grand narratives that have dominated the study of Jewish conversion in the 20th century: the dominance of martyrdom and forced conversions in Ashkenaz, contrasted with the role of rationalism and acculturation at the root of the inclination of Sephardic Jews towards conversion. It presents recent scholarly contributions towards the deconstruction of these narratives and discusses new directions of research into Jewish conversion, interpreting it as a metaphor for various theological concerns in Christian narratives, especially those found in anti-Jewish polemical literature. Finally, using the recent biography of Profayt Duran as a case in point, the article argues for the significance of studying religious conversion/apostasy beyond the confines of social dynamics or interreligious polemics between Jews and Christians. According to this view, the phenomenon of conversion and its representations in literature may also serve as a locus where cultural creativity, religious accommodation, identity formation and the marking of boundaries can all be studied fruitfully in the medieval context.