*Awkwardness* offers an account of the psychology and philosophical significance of a ubiquitous social phenomenon. Our aversion to awkwardness mirrors our desire for inclusion. This explains its power to influence and silence us: as social creatures, we don’t want to mark ourselves as outsiders. As a result, our fear of awkwardness inhibits critique and conversation, acting as an impediment to moral and social progress. Even the act of describing people as awkward exacerbates existing inequities, by consigning them to a social status that gives them less access to the social goods (knowledge, confidence, social esteem) needed to navigate potentially awkward situations. *Awkwardness* discusses how we ostracize and punish those who fail to fit into existing social categories; how we all depend on–and are limited by–social scripts and norms for guidance; and how these norms frequently let us down when we need them. But awkwardness has a positive side: it can highlight opportunities for moral and social improvement, by revealing areas where our social norms and scripts fail to meet our needs or have yet to catch up with changing social and moral realities. *Awkwardness* ultimately underscores the conflict between our moral motivations and our desire for social approval and conformity.