This study sought to better understand the relationship between affluence and elevated risk for psychosocial distress among adolescent girls. In-depth qualitative interviews at two time points with three cohorts of girls (sixth-, eighth-, and 10th grade; T1 n = 57, T2 n = 58) from two independent girls schools Grades 6 to 12, along with their parents, and their teachers were conducted. Through narrative thematic analysis, four overarching sources of significant stress were identified: (a) pervasive experiences of pressures to perform, (b) narrow constructions of success, (c) peer competition, and (d) misalignments in expectations between some girls and their parents. These pressures were even more heightened among the older girls. Although all of the girls reported experiencing these stressors, those girls who reported a more other-oriented sense of purpose also reported stronger connections with peers and seemed better able to manage the pressures.