This longitudinal study examined bidirectional paths between perceived parent-adolescent relationship quality and depressive symptoms, as well as the moderating role of sex, age, and personality type. 1313 Dutch adolescents (51% girls) from two cohorts (923 12-year olds and 390 16-year olds at Wave 1) reported on their personality, depressive symptoms, and perceived relationship quality to parents in four waves. Consistent with a relationship erosion perspective, depressive symptoms negatively predicted perceived relationship quality with parents. Relationship quality to mothers predicted depressive symptoms for boys and girls, but relationship quality to fathers predicted depressive symptoms only for boys. Personality type only moderated initial associations between relationship quality with mothers and depressive symptoms, which were stronger for Overcontrollers and Undercontrollers than for Resilients. Results thus reveal a pattern of mutual influence between perceived relationship quality and depressive symptoms that is moderated by the interplay among parent and adolescent sex and adolescent personality type.