This study aimed to evaluate changes in the attitudes of Japan's post-war youth towards gender equality and sexuality, and to examine whether these attitudes bore a relationship to school education. Different generations were delineated based on changes in courses of study and year of birth, and semi-structured interviews were conducted enquiring about experiences and opinions during secondary school days. We examined sexuality education in both junior high school (ages 12-15 years) and high school (15-18 years), views on premarital sex, views on marriage and divorce, and views on gender roles. Fifty-three survey participants were involved in the study: 30 women and 23 men. The characteristics of each generation were examined in relation to corresponding courses of study and the textbooks available in junior high and high schools, identifying both homologies and differences between the messages courses contained and the expressed beliefs of different generations of informants.