In two parts, this dissertation explores the nature and limits of empathy. In the first part, lessons are derived from studies of Adam Smith, David Hume, Michel de Montaigne, William Shakespeare, F. Scott Fitzgerald’s Jay Gatsby, and Barack Obama as well as from a concluding reflection on Stanislavsky based approaches to inhabiting a dramatic character. In the second part of the dissertation, the themes of the first part are explored creatively by way of a novel.