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A recent and understudied development in the systematic study of crime and deviance based on the rational choice theory of crime is the novel theoretical construct of thoughtfully reflective decision making (“TRDM”). Applied to the study of crime, the process of thoughtfully reflective decision making is important because offenders with difficulties in considering the consequences (i.e., costs and benefits) of their actions have been found to be more likely to engage in risky behaviors such as drug use, heavy alcohol drinking and delinquent acts. The present study explores more intricate theoretical relationships between TRDM and crime with negative binomial regression and structural equation modeling using data from the National Longitudinal Study of Adolescent Health to investigate the relationship between TRDM and property crime, violent crime and illicit drug use, while also testing for the presence of moderating effects of gender and peer influence on deviance, and mediating effects of TRDM on the relationship between self-control and crime. The results indicate that TRDM is a stronger predictor of less serious forms of deviance, among males and when levels of peer deviance are high, while TRDM partially mediates the effect of self-control on all three forms of deviance.