My dissertation argues that the romance genre, and in particular the character of Gawain, allowed English authors and audiences of the late middle ages (1350-1500) to negotiate new chivalric ideologies in response to broad social changes. In the midst of two major wars and a rapidly growing and upwardly mobile merchant class, the role of the knight in England shifted from the battlefield to the court. I examine the ways in which five Middle English romances, all of which feature Gawain, respond to these cultural changes. These romances date from the mid-fourteenth through the end of the fifteenth centuries and range from literary to popular, providing a broad overview of the many ways in which romance approaches the question of the role of prowess in chivalry. My examination reveals that the romances have a conflicted response to the loss of martial violence as the defining characteristic of a knight: the chivalry exercised primarily in courtly rather than military situations becomes a useful tool in building social relationships, but it also threatens to emasculate the male nobility and destabilize traditional social structures. By contrasting new cultural practices of chivalry with old literary ideals, the Gawain romances provide an ideal medium through which English society can explore the implications of adopting new chivalric ideologies and ultimately reformulate conceptions of chivalry that better reflect the changing role of the knight in late medieval society.