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This paper examines the negative relationship between thoughtfully reflective decision making (TRDM) and individual involvement in general delinquency. Parental attachment and family strain are considered as conditioning variables in this relationship. Specifically, using data from the National Longitudinal Study of Adolescent Health, this study assesses whether experiences of varying levels of parental attachment and family strain affect the TRDM/delinquency relationship. Results indicate that both parental attachment and family strain moderate this relationship, although conditioning effects are not in the expected direction. Explanations for these results are provided along with directions for future research on TRDM.