This phenomenological study examined the experiences of males aged 16-19 who self-identified as being alienated from their school system. Five participants engaged in three semi-structured interviews and one perception check. Descriptions revealed common themes throughout the structure of the experience. These themes were: (1) need to build relationships despite negative consequences, (2) loss of trust in school adults, and (3) fear of failure and of disappointing self and family. The invariant structure (essence) that emerged was the interrelationship among these themes as related to belonging, trust, and self-worth.