This article investigates the role of gender in educational choice-making for post secondary school destinations in contemporary Cyprus. More specifically, it examines the cultural and ideological mechanisms that produce gender differentiation in the way educational choices are made by secondary school students and their families. Drawing on evidence from a qualitative investigation of parents of students graduating from secondary schools it supports that the unequal patterns observed can be partly explained by the diverse ways Cypriot parents perceive gender roles which in turn influence their willingness to invest economic and non monetary resources to support their children's choices.