This study provides a test of how personality may shape social behaviors in a long-lasting dyad: the parent-adolescent relationship. In a large Belgian community sample, it was examined which parent Big Five characteristics were related to parenting and whether adolescent Big Five characteristics elicited certain parenting behaviors. Further, the proposition that individual differences are amplified under stress was examined by exploring whether parent personality was differentially related to parenting for parents of "easy" versus "difficult" adolescents. Moreover, possible differences in associations across parental and adolescent gender were explored. Mothers (N = 467) and fathers (N = 428) reported on their personality using the Five-Factor Personality Inventory; adolescents (N = 475) assessed their personality with the Hierarchical Personality Inventory for Children. Two types of parenting behaviors, overreactive discipline and warmth, were assessed 2 years later by parent self-reports, partner reports, and adolescent reports, from which multi-informant latent factors were created. Results indicate that parental personality was more relevant than adolescent personality for explaining overreactivity, but parent and adolescent personality were similarly relevant in explaining warmth. Especially parental and adolescent Agreeableness and adolescent Extraversion were important predictors of both types of parenting. Associations between parental personality and parenting were similarly related to parents of easy versus difficult adolescents, and for mothers and fathers parenting daughters or sons. Together, results show that parent characteristics as well as adolescent characteristics importantly affect dysfunctional and adaptive parenting.