Western discourses about young people and sexuality centre around the concept of risk. Anxieties have been fuelled by the increasing popularity of social media and practices such as 'sexting' and watching 'sexually explicit' materials online. Research has shown however that such risk discourses mainly serve to moralise about, pathologise and police particular behaviours and children. In order to counter such paternalism, researchers advocated a reconceptualisation of youth not as passive victims, but as active agents who actively negotiate sexual experiences and discourses. In this paper, which is based on ethnographic fieldwork among young people in The Netherlands, I argue that we need a reconceptualisation not only of youth, but also of their sexual practices, especially their online sexual practices. Mobilising an interdisciplinary interaction between critical socio-cultural studies of risk, feminist theory and adventure studies, I propose to reconceptualise these practices as 'adventures' rather than 'risky behaviour'. This opens up possibilities for a more reasoned analysis that acknowledges: (1) the distinction between risks and outcomes of an activity; (2) the constructive potential of risk; and (3) the subjective, dynamic character of risk and pleasure.