Currently, in Canada and elsewhere in the West, government spending, media, and health activities focus heavily on “lifestyles” and the “obesity epidemic.” In the last decade, many health and education professionals in Canada have adopted policies to improve health and fitness among youth, seeing them particularly “at risk” for engaging in unhealthy practices. Canada’s Vitality message of learning how to eat well, be active, and feel good about one’s self serves as the health promotion framework guiding our analysis of children’s constructions of health. Adults and youth readily identify with dominant health messages related to eating and being physically active but only rarely acknowledge any sense of embodiment or feeling good. Research with adults, embodiment, and health suggests that feeling good about one’s health and body is an impossible proposition as learning to care for the body is a constant and obligatory individual responsibility with limited possibilities of contentment. Health must be consistently and continuously worked at, making body-related projects a health imperative. We argue that learning how youth feel and experience health in relation to feeling good and pleasure is also imperative given the complex and contested relationships individuals have with health. Based on focus groups with 123 Grade 2 and Grade 4 students in Newfoundland, we use a feminist poststructuralist approach to examine how children understand healthy practices and messages about the ideal “healthy” body. A thematic and performance analysis combining talk, drawings, and talking about the artistic productions reveals children’s complicated relation to health and the body, where pleasure figures centrally and opens up possibilities for alternative conceptions of self and embodiment. We propose a serious investigation of children’s sense of pleasure and “having fun” as a fruitful avenue of research for critical scholars who aim to challenge dominant discourses of health and the body.