This article presents a model of the interrelationships between students' family, peer, and school worlds, and, in particular, how meanings and understandings derived from these worlds combine to affect students' engagement with schools and learning. In addition, the model focuses attention on students' perceptions of boundaries between worlds and adaptation strategies they employ to move from one context to another. We use a typology to illustrate four patterns we have found among 54 students in four desegregated high schools as they move across settings: (1) Congruent Worlds/Smooth Transitions; (2) Different Worlds/Boundary Crossings Managed; (3) Different Worlds/Boundary Crossings Hazardous; (4) Borders Impenetrable/Boundary Crossings Insurmountable. Unlike most other approaches, the model we present is generic. It transcends ethnic, achievement, and gender categories to consider multiple worlds, boundary crossings, and adaptation for all students.