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The adolescent brain is especially sensitive to rewards and peers, but cognitive systems of control do not develop until several years later. It is thus important for adolescents to avoid criminogenic-but-rewarding social contexts, including friendships with delinquent youth or risky activities with peers. Thoughtfully reflective decision-making (TRDM) is hypothesized to lead to more deliberate steps to shape social environments, and has been found to reduce delinquency in part through greater selection into prosocial capital, such as investments in education, hobbies, and caregiver relationships (Paternoster & Pogarky, 2009; Paternoster et al., 2011). In this project, I investigate whether thoughtful decision-making may likewise be positively associated with prosocial changes to social contexts that may reduce future crime among adolescents, and whether this depends on adolescent’s prior attitudes and expectations of rewards. Preliminary results using data from the PROSPER Peers project show evidence that TRDM is associated with making prosocial changes to one’s social context. I discuss implications for reducing adolescent delinquency through decision-making strategies.