<p>This study challenges the widespread view of adolescents as prominent risk-takers, by highlighting trajectories of engagement in both positive (few negative consequences, socially acceptable) and negative risk-taking (contravening standards, illegal). The objective is twofold: (1) to examine the evolution of engagement in both positive and negative risk-taking behaviors and their associated consequences; (2) to evaluate whether retrospective methodology provides a valid alternative to longitudinal studies for exploring intra-individual trajectories. Two samples were used: a cross-sectional comprising adolescents and young adults aged 10 to 25 years (Sample 1, <i>N</i> = 478, <i>M</i> = 15.47, <i>SD</i> = 3.06) and a retrospective involving young adults aged 18 to 27 years (Sample 2, <i>N</i> = 129, <i>M</i> = 21.87, <i>SD</i> = 1.74). Sample 1 responded to a questionnaire on engagement in two positive and two negative risk-taking behaviors, along with associated risks and benefits, while Sample 2 retrospectively answered the same questionnaire regarding their adolescent experiences. Findings demonstrate that: (1) Engagement in risk-taking differs across behaviors and aligns between cross-sectional and retrospective methods. Young adults recall higher negative risk-taking and lower positive risk-taking than current adolescents. (2) Perceived risks for negative risk-taking peaked in mid-adolescence, while perceived rewards followed a U-shaped trajectory, neither of which were reflected in retrospective accounts. (3) For positive risk-taking, perceived risks and rewards varied by behavior, and retrospective perceptions of rewards were consistent with cross-sectional findings. Retrospective methodology is suitable for studying intraindividual trajectories of risk-taking engagement and some perceived consequences, although it may be affected by retrospective bias.</p>