Adolescents’ behavior is often a matter of concern, given their increased likelihood of enacting antisocial behaviors, which cause disruptions in the social order and are potentially harmful for the adolescents themselves and for the people around them. In this six-wave longitudinal study we sought to examine the interplay among maternal empathy, multiple indicators of mother-adolescent relationship quality (i.e., balanced relatedness, conflict, and support), and adolescent antisocial behaviors rated both by adolescents and their mothers. Participants for the current study were 497 Dutch adolescents (56.9% males) followed from age 13 to 18, and their mothers. A series of cross-lagged panel models revealed reciprocal associations between maternal empathy and mother-adolescent relationship quality and between mother-adolescent relationship quality and adolescent antisocial behaviors. Interestingly, we also found some indirect effects of adolescent antisocial behaviors on maternal empathy mediated by mother-adolescent relationship quality. Overall, this study further highlights a process of reciprocal influences within mother-adolescent dyads.