The confrontation between modern and postmodern philosophical approaches is one of the most prominent and protracted academic debates of recent decades. In the philosophy of education, this debate has been ongoing since the 1980s and it continues to reverberate in contemporary discussions. One of the major themes of the debate is the endeavour of the modern philosophy of education to establish a universally valid rational foundation for educational theory and practice. This attempt has become a central target of criticism of the postmodern philosophies of education, which emphasize the contextual and situated nature of rationality and knowledge. As for the postmodern educational approaches, they have often been accused of giving rise to problematic forms of relativism. Rather than yielding fruitful solutions, the debate has largely resulted in an undesirable polarization between the modern and postmodern standpoints. This thesis seeks to take part in the discussion concerning the modernismpostmodernism debate from the viewpoint of Hans-Georg Gadamer’s (1900–2002) philosophical hermeneutics. The thesis consists of three interrelated studies that examine the relation of Gadamer’s hermeneutics to some of the prominent representatives of modernism (Jürgen Habermas) and postmodernism (John Caputo and Richard Rorty) from different perspectives. The common aim of these studies is to demonstrate that Gadamer’s philosophy is able to avoid some of the central philosophical problems and limitations associated with the aforementioned approaches and therefore it might also contribute to the movement beyond the unproductive modernism-postmodernism dichotomy in the philosophy of education.