This paper grew out of an exploratory study into the ways young people are using Social Networking Sites (SNS) and whether accessing potentially risky activities such as virtual gambling might encourage actual gambling or increase the likelihood of risky behaviour amongst younger users (aged 8–18). This work led to a wider examination of SNS as a form of leisure and the ways it has been adopted by young people and adapted for use in ways that are often dissimilar to those predicted by academics and social commentators. The paper consider the range of un-mediated content available via SNS to young people and how young people use this and associated self-generated content to explore various types of potentially risky behaviour.