This paper examines activist spaces for gender justice within two elite independent schools situated in an affluent part of the USA. Drawing on student interview data gathered as part of a broader study that sought to identify new educative approaches to addressing gendered violence, the paper explores attempts at these schools to engage boys in such spaces. With reference to two activist stories, the paper highlights the driving concern for including boys in discussions of gender justice (and, in particular, sexual misconduct and assault) as about ensuring their comfort. This concern is critically examined in light of the necessity of discomfort as central to gender transformative work. The paper examines how the emotional intensities of this work can both close down and open up conversations about gender justice and argues the significance of finding ways to support boys to critically explore these intensities towards engaging them in gender activism.