In this paper we want to rethink the educational significance of the novel – and particularly of novel-reading – from the perspective of a ‘meta-novelistic’ reading of Don Quixote, often acclaimed as the “first modern novel”. Our point of departure is double: on the one hand, there is the controversial contemporary phenomenon of “de-reading”, and all the educational discussions which it entails; on the other hand, there is the existing tradition of literary education, which, from different angles, has already extensively reflected upon the (moral, epistemological, ontological) relation between novel-reading, education and subjectification, but which also sometimes seems to have exhausted its means for doing so. To problematize this double starting point in a new way, we propose to revisit the ‘origins’ of the novel and novel-reading, at the dawn of modernity. By exploring the differences between the narratives of subjectification represented by the Cartesian cogito and Cervantes’ Don Quixote, which were near-contemporaries, we try to argue for an educational-philosophical rehabilitation of the latter, if not against then at least beyond the former. In a first movement, and in dialogue with novelists Milan Kundera and Carlos Fuentes, we do so by focusing on the novel as a particular form, or ‘configuration’, of knowledge – one that is by nature experimental and pluralist. In a second movement, we link this to Jean Baudrillard’s famous distinction between “simulation” and “illusion”, claiming that novel-reading qua subjectification always involves a Quixotic practice of adventurous, ‘playful’ and public negotiation between reality and its more or less ‘illusory’ alternatives.