A Trust Game was used to examine trust and reciprocity development in 12-18-year-old-adolescents (N = 496), as findings have been conflicting and transitions in adolescence remain elusive. Furthermore, this study tested the roles of gender, risk, and individual differences in empathy, impulsivity, and antisocial tendencies in trust and reciprocity. Results indicate stability in trust and a decrease in reciprocity across adolescence, but also show that trust and reciprocity choices were influenced by risk, and that empathy mediated the age-related decrease in reciprocity. Males trusted more than females, but there were no gender differences in reciprocity. These findings highlight the importance of considering individual differences and adolescents' sensitivities to varying contexts in explaining trust and reciprocity development in adolescence.