This paper examines the facilitation of a gender transformative program operating in the USA with groups of disadvantaged young men and boys. The program engages young men in reflecting on the impacts of harmful gender norms. The paper presents two stories of facilitation that explore issues of sexual consent and gendered emotions. These stories illustrate an approach to teaching for empathy that is common to gender transformative programs where the focus is on encouraging boys and men to consider the suffering of girls and women. They also illustrate the discomfort involved in such teaching when boys and men are confronted with their complicity in this suffering. Drawing on key feminist work, the paper highlights the possibilities and limits of a pedagogy of empathy for gender transformation. Recognizing that one can never really know the other, it argues the significance of engaging boys and men in critical self-reflection on the limits of their understandings of themselves and others. Such self-reflection is not about doing away with attempts to empathize but about acknowledging these attempts as limited by the very terms through which we make ourselves and others intelligible and the reality that some aspects of ourselves and others may remain unknowable.