In this thesis I argue literary readership allows us to gain imagined experiences necessary to sympathize with people whose experiences are different from our own. I begin with a discussion of Adam Smith’s conception of sympathy and moral education. Although sympathy is a process we take part in naturally as members of a society, we can only be skilled spectators if we practice taking the position of the impartial spectator and critically reflect on our judgments. As I will argue in this thesis, literature provides a way for us to practice spectatorship without the consequences that come along with making mistakes when judging real people. Literature also provides a way to build up a stock of experiences, which can be applied together with our personal life histories to create the most informed judgments possible.