Age-disparate sex is associated with increased HIV risk among adolescent girls and young women (AGYW) in sub-Saharan Africa. However, little has been done to understand the dynamics of such relationships from the perspectives of either AGYW or older men, and the communities in which these relationships are embedded. This article explores the motivations and perceived benefits of such relationships for AGYW and older men, plus the social and sexual and reproductive health (SRH) consequences. It reports findings from participatory focus group discussions and in-depth interviews with young people aged 14–24 and adult community members aged 25–49 in rural and urban Tanzania and Uganda.