Abstract This article describes a qualitative study examining two interrelated facets of the school-to-work transition among urban high school students: their relationships with important adults within that transition and the ways they experience the subjective aspects of social class and class-related constructs in those relationships. Participants were 27 urban adolescents participating in a school-to-work program or otherwise employed after school. We analyzed data generated from participants’ elaborations on their scaled responses to adapted Relational Health Index items pertaining to supervisors and other important adults at work. Qualitative analysis identified four thematic categories of how social class is experienced in urban adolescents’ relationships at work: Navigation of Identity; Perceptions of Similarity, Difference, and Being Understood; Receipt of Mobility Encouragement; and Awareness of Stratification. Results suggest that the first two of these categories represent the ways that participants work to find balance between the dual realities of Mobility and Stratification.