In Ontario, Canada, adolescent boys are increasingly developing a disinterest towards health and physical education (HPE) class, and also are withdrawing from HPE as soon as they institutionally are allowed to do so. To date however, there has been a dearth of research that has explored the various mechanisms that are dissuading boys from active participation, and prompting boys to develop a cultural disaffection towards HPE. Drawing on data from an ethnographic case study, this paper begins to provide some insights in further understanding the emerging disaffection towards HPE, and increasing attrition rates among Canadian boys. As illustrated in the study findings, this paper suggests that boys who disengage from HPE do so not because they are genetically predisposed to be lazy, or are unmotivated. Rather, their repeated experiences of explicit and symbolic abuse, degradation, and ignominy from teachers and peers alike dissuade them from active HPE participation. The findings of this study suggest the need for teachers to initiate a reflexive stance in their teaching practices, while concomitantly teaching students critical health literacy skills in an effort to meet the health and well-being needs of adolescent boys.