Seven features of adolescents' relationships with mothers and with fathers (time together per day, number of activities, degree of influence, subjective closeness, and frequency of experiencing positive, hostile, and sad emotions in the relationship) were used to predict adolescents' problem behavior and chemical use. Using a sample of 64 seventh- and 43 tenth-grade adolescents and self-report questionnaires, this study: (1) examined age differences in these features of mother-adolescent and father-adolescent relationships; and (2) investigated whether features of relationships with mothers and with fathers predict adolescents' problem behavior and chemical use. Adolescents' reports of hostile emotions experienced in relationships with mothers and with fathers were significant correlates and predictors of problem behavior and chemical use. For adolescents in both grades, features of relationships with mothers explained more variability in reports of problem behavior. Further, lower levels of parental influence were associated with and predictive of higher levels of problem behavior and chemical use in the tenth-grade sample. These findings suggest that intervention that is targeted at assisting parents in developing and maintaining a less hostile, more positive, active, and supportive parent-adolescent relationship may be warranted. (Author/EV)