This article explores upper secondary school students’ understandings and experiences of health in Denmark, where public health promotions appeal to pleasure. Health promotion thereby taps into capitalist society's ‘imperative of enjoyment’, which reproduces ideological fantasies about the fulfilment of desires through the consumption of health. Based on qualitative empirical material produced through participatory and visual methods during fieldwork conducted in 2012, the analysis shows that relations between healthiness and pleasure are conflated and paradoxical: the students try to fit into society not only by being healthy, but also by enjoying healthiness; but if they fail pleasure, they fail healthiness and experience a loss of individual social value. Although the ‘enjoyment society’ has the potential to produce individualisation and marginalisation, the students in this study actively attempt to subvert its double bind by insisting that collective experiences with peers constitutes the foundation of enjoyable healthiness. Nevertheless, public health promotions that reproduce enjoyment as an imperative, even in the pursuit of health, risk reinforcing young people's resistance towards health.