Gender equality is one the grounding principles of general education. Many international studies, however, show that the school context reproduces both gender stereotypes and gendered self-positioning. The article studies how boys and girls from Estonian schools of general education perceive different aspects of school as well as themselves, their opportunities and the limits of permissible within the school. The study of high school students conducted within the program “Gender Equality and Life-Work Balance”, funded by Norway Grants, elicited responses from 649 students that provided a multi-layered picture of students’ gender-marked perceptions of the school and the effect of gender stereotypes on students’ self-perception as students. The theoretical framework of the article introduces the notion of social grammar that links gender and school roles into a unified pattern of behaviour. The material was analysed with the help of thematic qualitative content analysis. The discussion takes a closer look at the similarities and differences in the opinions of respondents of both genders, their self-positioning as the creator- subject of actions and changes as well as the limits of freedom and the permissible. We conclude that, as the result of gender stereotypes, students’ descriptions of school contain more references to gender differences than gender similarities, which culminates in the descriptions of what is normal for both genders. However, the shared role of the student also unites students’ desire for change at school. The neoliberal agenda has not added gender equality to schools.