This retrospective study sketched the educational pathways of two seniors attending an alternative high school in an attempt to discern how relational identities of students, families, and educators are defining forces of such pathways. Cumulative school records and special education files were triangulated with interviews of the students, their guardians, and school personnel, beginning with students' entry into preschool. Events, decisions, and experiences that shaped students' educational pathways were identified. The interpretive reading of the data revealed the interplay among students', educators', and families' identities and how they sustained, diverted, and redirected the journeys of participating students. Educators are called to be facilitators in the interplays among the student, school, and family identities through the development of committed relationships in school environments. Educators are critical mediators who can help students build resilience against stressors, a sense of belonging, and responsibility for creating lived trajectories that are personally and socially fulfilling. (Contains 3 notes and 2 figures.)