Adolescence is a phase of heightened risk taking compared to childhood and adulthood, which is even more prominent for specific populations, such as youth with attention-deficit/hyperactivity disorder (ADHD). Little is known about how perceived risks and benefits relate to adolescent risk taking. Here, we used the adolescent version of the Domain-Specific Risk-Taking (DOSPERT) scale to investigate risk taking, perceived risks, perceived benefits, in two studies. In the first longitudinal study, 375 11-to-23-year-olds completed the DOSPERT one up to three times. A second biannual longitudinal study included 180 11-to-20-year-old boys with ADHD (N=81), and matched controls (N=99). Using mixed-effects models, we found a peak in risk taking in mid-to-late adolescence in the first study in the health/safety and ethical domains, with similar curvilinear patterns in perceived benefits (peaks) and perceived risks (dips). Age-related changes in risk taking, risk perception, and benefit perception were also observed in the ADHD-control sample with comparable patterns in both groups. Interestingly, in both studies risk-return models indicated that perceived benefits related more strongly to risk taking than perceived risks, and perceived recreational benefits increasingly related to recreational risk taking with age. Moreover, in the social domain, perceived risks of adolescents with ADHD related less strongly to their social risk than matched controls. Our results are consistent with elevated levels of risk taking in real life and highlight the role of perceived risks and benefits in risk taking. These findings provide tentative entry points for prevention and intervention.