In this article I explore some points of convergence between Habermas and Derrida that revolve around the intersection of ethical and epistemological issues in dialogue. After some preliminary remarks on how dialogue and language are viewed by Habermas and Derrida as standpoints for departing from the philosophy of consciousness and from logocentric metaphysics, I cite the main points of a classroom dialogue in order to illustrate the way in which the ideas of Habermas and Derrida are sometimes received as well as the actual relevance of ethical and epistemic concerns within educational settings. I claim that such concerns cannot be sidestepped without cost and that they can be approached by combining rather than rigidly separating Habermas and Derrida. Beyond the consolidated polemics, emancipatory politics and Enlightenment priorities of truth and justice bring Habermasian reconstruction and Derridean deconstruction closer than it is typically assumed. Attention to such a convergence can enrich the teaching material of higher education courses which usually comprises either Habermasian or Derridean texts but rarely both. It can also stave off some of the risks involved in some versions of constructivism as they occur in school practice.