The high-poverty urban school building is a prime environment for racial misunderstanding between teenagers and adults: most teachers are white and middle class, while most students are nonwhite and live near the poverty line. In this reflective essay, Jay Wamsted, a white teacher, examines the complicated nature of a teacher-student relationship in one such school. He uses a story of a hallway incident as a frame for examining his time spent teaching a young, black male student, and in doing so he demonstrates both successes and missteps, providing a window into the various interpersonal challenges facing the teacher in the high-poverty urban school.