We are in the midst of a boy crisis. Statistics and cultural observations indicate that there are a myriad of problems in health, education, the workforce, etc., which are having a disproportionate effect on men. At the heart of the boy crisis is a loss of purpose, as men no longer have a clear social role, drawn from their identity as soldier, leader, and sole breadwinner. To make sense of this cultural moment, I reach back to Plato, who lived in the midst of a boy crisis in the fifth century B.C. Athens. Through philosophy, Plato clarified the concept of masculinity and the virtue of courage, rooted in truth and goodness. I close-read Plato's Republic, defending his definition of courage as the act of preserving through everything the beliefs that the lawgiver declared ought to be feared through the process of education. I offer a philosophical response to the boy crisis and call for a cultural consensus and clear societal standards by which boys can find and preserve their sense of purpose. Without courage well-conceived and well-expressed, both individuals and society suffer. I present case studies from in-depth field interviews I conducted with members of Courage International, a Catholic ministry that works with those experiencing same-sex attraction. Through these case studies, I document the unique experiences of two Courage members and a priest working as the organization’s associate director to illuminate Plato's conception of courage, masculinity, and the common good at work in the lives of contemporary American men.