Masculinity studies in Africa have often highlighted young men’s tendencies to be dominant, violent, and selfish in relation to female peers. This article introduces the concept of “philogynous masculinities” as part of an exploration of more gender equitable tendencies among young men in secondary schools in Maputo, the capital of Mozambique. Findings from fieldwork in schools and student’s neighborhoods reveal that understanding alternative notions of manhood requires sensitivity to the contexts in which these are accentuated. While the bom pico notion, stressing men’s sexual satisfaction of women, received emphasis in the context of sex education, the ndota notion of restraint and antiviolence was activated under homely circumstances. Discussing multiple male subjectivities across contexts rather than classifying individual men allows for alternative configurations without ignoring their contradictory manifestations. The article urges masculinity studies to move beyond dichotomies between modern and traditional forms and to explore entanglements of hegemonic and alternative masculinities.