Spenser’s poetry offers a glimpse into the aesthetics of skepticism. To understand Spenser’s exploration of perception, interpretation, and subjective experience, the chapter considers skeptical questions posed by medieval philosophy regarding universals, abstraction, mental language, the status of pictures in the mind, and the extent of God’s power. According to Heiko Oberman’s view of the via moderna, these nominalist investigations with their counterfactual approach lead to feelings of contingency and autonomy that in turn produce the subversive political idea that things can be otherwise. In his translations of du Bellay and Marot in his Complaints and in “November,” as well as on Mount Acidale in The Fairy Queen and in The Mutability Cantos, Spenser creates rapturous visions that soon dissolve. These intimations of the sublime have a skeptical quality that suggest a grounding in nominalism. Because Heidegger combats a skeptical metaphysics premised on the rift between subject and object, this chapter uses aspects of his philosophical lexicon to illuminate the stakes of Spenser’s poetic travail with problems of truth, concealment, disclosure, and fullness of being.