This paper analyses the trope tante girang (cougar) as a way to criticise gender relations and modernity. The first novel is Tante Girang by novelist-turned filmmaker Ali Shahab and the second one is Cross Mama by Motinggo Busye, a name famously known for writing erotica. Both novels were published in 1968, a significant year in Indonesian history as the nation underwent a major transition to the New Order regime. In these novels, loneliness and isolation from family connect mature women and rebellious young men where they take risks in sexual adventures. By taking the historical context into account, I argue that tante girang manifests as both sexual and pedagogical fantasy that challenges the established institutions and the pursuit of modern happiness.