The study of contemporary youth gender cultures within an educational context illustrates the emergence of new possibilities of self-expression as well as more favourable attitudes towards diversity, at a time when stereotypical gender mandates still persist. This study aimed to deepen understanding of gender identity construction by analysing conversations with 14 students in a secondary school on the southern outskirts of the Community of Madrid. The selected students stood out among the rest due to a combination of high social status and an understanding of gender categories as less stereotyped and rigid. Analysis showed how monoglossic meanings may be confronted by experience within one's close environment--that contradicts or reaffirms the norm, as well as by personal beliefs and desires. The result is a complex process of adjustment, which swings between believing in individual choice, personal experiences of inequality, and the need to feel part of the group.