We report a study that examined the existence of a cognitive developmental paradox in the counterfactual evaluation of decision-making outcomes. According to this paradox adolescents and young adults could be able to apply counterfactual reasoning and, yet, their counterfactual evaluation of outcomes could be biased in a salient socio-emotional context. To this aim, we analyzed the impact of health and social feedback on the counterfactual evaluation of outcomes in a laboratory decision-making task involving short narratives with the presence of peers. Forty risky (eg, taking or refusing a drug), forty neutral decisions (eg, eating a hamburger or a hotdog), and emotions felt following positive or negative outcomes were examined in 256 early, mid-and late adolescents, and young adults, evenly distributed. Results showed that emotional ratings to negative outcomes (regret and disappointment) but not to positive outcomes (relief and elation) were attenuated when feedback was provided. Evidence of development of cognitive decision-making capacities did also exist, as the capacity to perform faster emotional ratings and to differentially allocate more resources to the elaboration of emotional ratings when no feedback information was available increased with age. Overall, we interpret these findings as challenging the traditional cognitive developmental assumption that development necessarily proceeds from lesser to greater capacities, reflecting the impact of socio-emotional processes that could bias the counterfactual evaluation of social decision-making outcomes.