This research was motivated by concerns about the consistent pattern of poor retention of some boys to Year 12, and overall poor performance of some boys in Australian schools. This study broadly drew on critical discourse theory to examine the circumstances surrounding the decision to leave school by 22 boys from three different geographical locations i.e. provincial, rural and metropolitan, in Queensland, Australia. Adopting Fairclough's (2002) model of discourse as a conceptual framework for this research allowed the exploration of the different socio-cultural practices as perceived by the boys in their geographical location. Similarities in the boys' narratives included their belief in the value of learning, and that the context of school was unable to provide them with learning that was both meaningful and relevant to their post school pathways. Despite the similarity of the boys' school experiences, the range of storylines they chose to illustrate their experiences in their geographical context differed. The study concluded that consideration be given by education researchers to the construction of a dominant masculinities discourse in different geographical locations, when exploring boys' engagement with school.