Over the last decade, the relationship between boys, young men and sex and relationships education (SRE) is one that has been characterised by a history of problematising. One of the main difficulties lies with young men's engagement with the subject, and in this article I make a retrospective examination of recent classroom experience with young people and training with professionals who deliver SRE. In the exploration of how best to engage this client group, I argue that masculinity and sexuality are potent issues in their lives and an understanding of these helps explain patterns in young men's behaviour, sexual health and attitudes towards SRE. Autoethnography is used as a method of enquiry to produce short vignettes in which I evaluate my successes and failures with four different boys and young men in terms of engagement. From these primary data, I have distilled four key domains in the form of a framework that I offer as a springboard for researchers, policy-makers and practitioners to consider more positive implications for future practice.