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Using a narrative methodology, this paper explores the dilemmas novice teachers in urban schools encounter as they cross race and class lines to get to know their students.. Many teachers who begin their career wanting to teach in an urban setting have not spent time in urban schools and have relatively little knowledge about the lives of children and youth who live there. This lack of experience challenges the novice teacher working to develop positive, productive relationships with students. The paper draws on five exemplary dilemma narratives written by novices in urban schools and highlights how and why new teachers in this setting struggle to feel confident in their role as teacher of the children they want to serve.