Internationally, the research on the education of boys has sought to understand how social practices, behaviours and rituals contribute to identity construction. We are interested in approaches to the emotional labor of doing 'boy work'. As educators grapple with the gendered performances and subjectivities of young men, there is an imperative to engage with the affective dimensions of boyhood. We explore what theories of affect can add to our understandings of masculinities and masculine identity practices in rapidly changing affective economies of gender and, specifically, what this may mean for relationships formed between educators and students. To illustrate how theories of affect can open up new analytical spaces, we present two vignettes from a program in the United States designed to support young men and boys to gain critical awareness of restrictive 'gender norms'. Drawing primarily upon Ahmed's work on affective economies, we theorize how attention to "affective economies of boyhood" can positively influence the work of educators today.