This study explored whether differences between siblings’ personal characteristics (as measured in the domains of risky behavior, peer competence, and academic achievement) were linked to levels of intimacy in each sibling’s mother- and father-child relationships. Participants were parents and first- and second-borns from 191 White, middle/working class families. OLS regression models that included measures of both adolescents’ individual functioning and sibling differences in functioning as predictors produced significant results for linkages between sibling differences in risky behavior, peer competence and GPA and intimacy in parent-child relationships, with significant effects for four of twelve models. For example, firstborns who reported less risky behavior relative to their siblings reported higher intimacy in their relationships with their fathers. In most cases, however, the direction of this effect differed from what was predicted in showing that siblings with poorer functioning than their siblings reported more intimacy with parents. Results were discussed in terms of potential compensation processes.