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Much scholarship on Shakespearean skepticism has focused on the tragic, regarding skepticism as a destabilizing, anxiety-provoking force. Conversely, I will argue that Pyrrhonism—a model of skepticism available to early modern readers, which encourages thinkers to accept multiple interpretations in order to arrive at a state of tranquility—offers an alternative that enriches the models of tragic skepticism advanced by scholars like Stanley Cavell. Analyzing Shakespeare’s sonnets, I argue that Shakespeare encourages readers to feel their own isolation from other minds, not as an experience of anxiety, but rather as a source of pleasure. Shakespeare uses metaphor to expose and explore the instability of meaning and the unreliability of an image to signify consistently. In place of epistemological certainty, Shakespeare offers his readers a model of collaborative meaning-making, where readers are invited to accept multiple interpretations of a given theme or image as possibly true.