The study investigates the gender stereotypes about the choices between family and career, among a group of teenagers in the province of Pesaro Urbino, Marche Region, Italy. Therefore the gender constructions and the relationship between women and men are analysed in the framework of data concerning the decline of female employment in the area as well as previous work highlighting the dominant gender asymmetric role distribution. The teenagers’ opinions bring to light deep gender stereotypes among the majority of interviewees. At the same time only a minority puts in discussion the hegemonic masculinity and the social disadvantage of women. Since gender role reproduction is the result of interaction between each individual agency and the framework of his/her action, the structure, to reshape the relationship between masculinity and femininity would require an institutional and specific policy long term cultural investment in order to arise consciousness around gender inequality and its impact on opportunities. So, the school would play a crucial role as education and socialization privileged context.