This paper examines students' evolving cross-group relationships in a comprehensive high school in Baltimore County, Maryland, USA, between 1950 and 2000. The findings of this research, situated at the intersections of two lenses of inquiry: oral historical analysis and critical studies, uncover both the power of students accustomed to integrated spaces to break social barriers in spite of institutionally entrenched segregating norms; and the power of institutional norms to segregate students when major demographic shifts bring into institutional parameters youth unaccustomed to integrated spaces and diversity. (Contains 2 tables and 54 notes.)