Schools have long played a significant role in teaching students the values of gender respect and equity. These values have been embedded in education policy and practice in contexts such as Australia for decades. In the current #MeToo moment, there has been renewed emphasis on gender transformative teaching in schools. This work, however, is difficult and discomforting especially in relation to problematising issues of masculine entitlement with boys. The complexities and intensities of emotion associated with this discomfort are the focus of this paper. The paper considers three areas that are important for educators to contemplate in how they approach this work: (1) the significance of pedagogic discomfort; (2) the pedagogical principle of mutual vulnerability; and (3) the value of strategic empathy and ethical self-reflection. These areas of focus are central to engaging boys in gender transformative pedagogy and are particularly important given the broader backlash context against feminism.