The critical resources furnished by deconstruction have more than occasionally been turned with negative effect on traditional and more recent conceptions of liberal learning, including the reaffirmation of the humanities associated with philosophical hermeneutics. The first two sections of the paper review the contrasting and mutually opposed stances towards learning represented by early formulations of deconstruction and of hermeneutics. An exploration is then undertaken in the later sections of developments that have taken place in both deconstruction and hermeneutics since the Derrida-Gadamer encounter in Paris in 1981. While not in any sense assimilating hermeneutics to deconstruction or vice versa, this exploration identifies significant shifts in later formulations of both which provide a more inclusive context for understanding learning as a human undertaking, including the identification of tensions that are more promising than negative.