This reflective paper explores the emotions, ethics, and challenges of facilitating training for youth practitioners to tackle gender-related violence (GRV). This paper draws on insights from a training intervention that emerged from an EU-funded feminist project (UK GAPWORK project), which sought to bring together approaches to tackle violence against women and girls with challenging heteronormativity and homophobia. Drawing on accounts from facilitators and participants, the aim of this paper is to identify tensions, opportunities and strategies in developing training to support critically engaged practice around sensitive topics such as GRV, and to consider the significance of working with discomfort within any such training intervention. We reflect on how discomfort presented within the training space and the challenges presented. This paper examines how Boler's theoretical work on pedagogy of discomfort can be operationalised to think productively about designing and delivering training for informal educators on sensitive issues with ethical integrity.