This session focusses on engaging students and boys in particular, to reflect on and critically examine masculinities in school. While social influencers like Andrew Tate may be appealing and reaffirming for boys feeling “lost” and unsure about how to “be boys”, we show the power of self-reflection possible among all students to disrupt and challenge masculinity. Drawing on past workshop experience and research in Critical Masculinities in Education, we offer examples of activities used during middle-school workshops. The primary objective is to examine the voices and experiences of students (13-15 y.o.) as they reflect on issues of masculinity, misogyny, sexism, and healthy relationships. We consider what and how silences around masculinities and gender might be addressed to create healthier, safer learning environments for all students.