This study seeks to understand boys' lower academic success by analysing the relationship between sex, gender role self-concept, help seeking attitudes, and school performance in a sample of 182 German 11th grade students (83 girls, 99 boys), age 16. Grades at two points in time, intelligence test data, help-seeking attitudes, gender role self-concept (including socially desirable and socially undesirable masculine and feminine traits) were assessed. Controlling for intelligence, girls achieved better grades than boys. Girls reported more positive attitudes towards help seeking than boys. Positive femininity related positively, negative masculinity negatively, to help seeking. Negative masculinity mediated the relation between sex and grades. Mediation analyses focusing on change in school performance revealed that the influence of negative masculinity on boys' impairment in grades was partly explained by negative attitudes toward seeking help. Results are discussed with regard to the impact of a masculine gender role self-concept on academic help seeking. (Contains 4 tables.)