During adolescence the prevalence of certain health risk behaviours, such as binge drinking and illicit substance use, increases. Engagement in these behaviours has been attributed to immature self-regulation, heightened sensation seeking, and peer influence during adolescence. However, more recently, adolescence has been characterised as a time of risk sensitivity rather than universal increases in health-risk behaviour. For example, the extent to which individuals engage in health-risk behaviours may relate to their sensitivity to the social risk involved in engaging in the health-risk behaviour. In the present study we examined how individual differences in social risk perception relate to an individual’s expectation of future involvement in risky behaviour during adolescence. One hundred and twenty-two participants (ages 11-17, mean 14 years) reported their expected involvement in a number of risk behaviours and degree to which they thought a) engaging in these behaviours would make people like them more, and b) not engaging in these behaviours would make people like them less. Social risk perception was operationalised as the perceived social benefit gained from engaging in a risk behaviour, from low (people would like you less), to high (people would like you more). We used linear mixed effects modelling to assess the contribution of social risk perception in predicting individuals expected involvement in health risk behaviours. We found that adolescents who perceived the social benefit associated with engaging in a risk behaviour to be high were more likely to report higher expected involvement in said behaviour. This was true for illicit substance use, aggressive and illegal behaviours, and risky drinking, but not for risky sex. Adolescents who reported a higher degree of peer victimisation showed a stronger relationship between the perceived social benefit of engaging in, and expected involvement in, these risk behaviours. Further, perceived social benefit moderated the relationship between sensation seeking and expected involvement in risky behaviours. Taken together, these data suggest that, across a number of health risking behaviours, adolescents incorporate perceptions of social risk when making decisions regarding their expected involvement. We argue that future investigations of adolescent health risking behaviours should incorporate social risk.