It has been assumed that adolescents increase risk-taking tendencies when peers are present but findings on experimental decision-making have been inconclusive. Most studies focus on risk-taking tendencies, ignoring the effects peer presence can exert over other cognitive processes involved in decision-making, as well as any other underlying developmental and individual differences. In the present study, the trial-by-trial choice behavior was analyzed in a task in which adolescents adjust to dynamically changing risk probabilities. Using Bayesian modeling, the study aimed to infer about peer presence effects on risk-taking tendencies but also on reactions to, exploration of, and learning from positive and negative outcomes of risk-taking. 184 pre- to late adolescents (M = 14.09 years, min = 8.59, max = 18.97, SD = 2.95, 47% female) conducted the Balloon Analog Risk Task under two conditions: Once alone and once in the presence of a (non-existent) peer observing them virtually. Findings revealed that (a) peer observation reduced risk-taking but increased exploration tendencies and (b) that individual differences modulated this effect. Especially female pre-adolescents increased their openness to explore different choice outcomes when a peer observed their behavior. These results support the assumption that the occurrence and direction of peer influences on risk-taking depend on a person-environment interaction, emphasizing the dynamic role peers play in adolescent risk-taking.