As a way of participating in the discussion on the disciplinary nature of philosophy of education, this article attempts to find another distinctive way of relating philosophy to education for the studies in philosophy of education. Recasting philosophical skepticism, which has been dismissed by Dewey and Rorty in their critiques of modern epistemology, it explores whether Cavell's romantic interpretation of it can allow us to conceive of skepticism as an exemplary practice of education, especially internal to the learner. This opens up the possibility of viewing the disciplinary nature of philosophy of education as congenial to other humanities like literature or religious studies, rather than to social sciences as usually considered.