In this dissertation, I examine the influence of Pyrrhonist skepticism over Shakespeare’s sonnets. Unlike academic skepticism, which begins from a position of doubt, Pyrrhonist skepticism encourages an embrace of multiple perspectives that, according to Sextus Empiricus, leads first to a suspension of judgment and ultimately to a state of tranquility. The Pyrrhonian inflection of Shakespeare’s sonnets accounts for the pleasure and uncertainty they cultivate in readers. By offering readers multiple perspectives on a given issue, such as love or infidelity, Shakespeare’s sonnets demonstrate the instability of information, suggesting that such instability can be a source for pleasure. One essential tool for the uncertainty in the sonnets, I argue, is the figurative language they draw from a variety of fields and discourses. When these metaphors contradict one another, creating fragmented images in the minds of readers, they generate a unique aesthetic experience, which creates meaning that transcends the significance of any of the individual metaphors. In the first two chapters, I identify important contexts for Shakespeare’s sensitivity to the pliability of figurative language: Reformation-era religious tracts and pamphleteers’ debates about the value and function of the theater. In Chapter 3, I examine Shakespeare’s response to the Petrarchan tradition, arguing that he diverges from the sonneteers, who often use figurative language in an attempt to access and communicate stable truths. Shakespeare creates epistemological instability in sonnets both to the young man and to the dark lady, and, as I argue in Chapter 4, this similarity offers readers an opportunity to think beyond traditional divisions between the two sonnet subsequences.