A challenge for history education in Sweden involves integrating questions regarding relationships and sex education. The purpose of this article is to explore how students and teachers relate historical narratives about women’s sexuality between the past and present, with a particular focus on students’ discussion of shame. To analyse shame as something beyond the individual, we focus on the interrelationship of gender, sexuality and shame. The study builds on a poststructural understanding of gender, norms, sexuality and subjectification. The data comprise video-recorded classroom observations, focus group interviews with 16–19-year-old students, and interviews with their teachers. The findings are structured into two themes: shame as regulating women’s sexuality, and sexualised shame as a historical continuity. We conclude that it is highly challenging for a history teacher to construe a classroom environment that breaks with traditional historiography without resorting to a fragmentation of history into isolated case studies of the spectacular.