Adolescence is a formative period of identity development. From the start of high school young people begin to direct their own development through peer selection and behavioural choices. During this time young people have the opportunity to engage in risky behaviours such as drinking alcohol, smoking, having unprotected sex and taking illegal drugs, for the first time. These behaviours amongst young people have been linked to a range of adverse health and wellbeing outcomes, both short and long term. This study seeks to improve understanding of eleven to fifteen year olds' behavioural choices through investigation of potential links to perceptions of adulthood and gender. In order to capture this more fully a mixed methods approach is used with a quantitative cross-sectional pupil survey and in-depth intergenerational family qualitative interviews. By exploring a broad range of age and gender stereotyped, and risky behaviours, this study seeks to provide better understanding of participants' perceptions, motivations and involvement in these behaviours. Results of the study demonstrate both gendered and age differentiated patterns of perceptions. Between eleven and fifteen years old, boys demonstrate more pronounced values attributed to masculine roles. Conversely, stereotyped feminine roles appear to decrease in appeal to girls. Fourth year girls perceive risky behaviours as considerably more relevant to them, than their male peers. Interviewed mothers were unsure of how best to manage their daughter's behaviours considering their own lack of experience and the apparently high value attributed to non-confrontational, friendship based, mothering. Current methods of teaching and intervening generally address mixed gender age-group classes. This research suggests in order to modify risk-taking behaviours a gender specific approach may be more effective.