This volume presents a series of essays in honor of noted scholar of political theory, Mary P. Nichols. The essays reflect Nichols’ pathbreaking work in ancient Greek political thought, as well as her influential treatments of works of literature and film in conversation with political theory. Part I: Conversations Concerning Love and Friendship features essays about the philosophical meaning of human connection and affection. Part II: Conversations Between Politics and Poetry looks at the political significance of art, and the ways in which political rule can be understood to be artistic or poetic. Part III: Conversations from Tragedy to Comedy considers whether the human need for community is something to be lamented or celebrated. Broad in scope and interdisciplinary in approach, the essays in this volume address authors such as Plato, Aristotle, Shakespeare, Machiavelli, Mary Wollstonecraft, G.W.F. Hegel, Jane Austen, Henry James, William Faulkner, Albert Camus, J.R.R. Tolkien, and Aleksander Solzhenitsyn, as well as the films of Woody Allen and Whit Stillman.