From conception to death, helping relationships promote positive development and enable people to surmount challenges in their lives. Is it the case that the negative consequences of a genetic propensity for risky behaviors can be attenuated by helping relationships (a G × E)? But is it also the case that people with such a genetic propensity are less likely to have helping relationships compared to people without such a propensity (a rGE)? We illustrate this complex pattern of gene–environment interplay by drawing on the National Longitudinal Study of Adolescent Health and a combinatoric analytic strategy. We focus on a gene associated with dopamine receptor type 2 (DRD2 TaqIA), student–mentor relationships, and educational continuation beyond secondary school. Results reveal that, for both white and black males, DRD2 A1+ (A1A1 and A1A2 genotypes) is associated with a decreased likelihood of school continuation compared to their counterparts with DRD2 A1–; mentors who are teachers compensate for this negative association (a G × E); and youth with DRD2 A1+ are less likely to have a mentor who is a teacher than their counterparts with DRD2 A1– (a rGE).