Out of school youth (OSY) are adolescents who have not completed their schooling and are not currently enrolled in school. This study sought to understand why learners drop out of school by interviewing 41 OSY (aged 13-20 years). Respondent Driven Sampling was used to recruit OSY. Content analysis was used to analyze the data. Gender differences were found in the reasons for leaving school. Males dropped out due to poor school performance, vocational aspirations, and social interactions at school. Females dropped out due to family-related reasons. In males and females, friends played a role in students dropping out of school. Participants who performed well academically left school to be with their OSY friends. Those who did not pass and had friends who progressed to the next grade also dropped out of school. Preventing students from early school leaving involves targeting the interpersonal, school and policy levels with gender-specific intervention.