Concurrent and longitudinal relations among parental emotional expressivity, children's sympathy and children's prosocial behavior were assessed with correlations and structural equation modeling when the children were 55-97 months old (N = 214; M age = 73 months, SD = 9.59) and eight years later (N = 130; ages 150-195 months old, M = 171 months, SD = 10.01). Parent emotional expressivity (positive and negative) and children's sympathy were stable across time and early parent-reported sympathy predicted adolescents' sympathy and prosocial behavior. Parents' positive expressivity was positively related to sympathy and prosocial behavior, but in adolescence, this was likely primarily because of consistency over time. Early observed parental negative expressivity was negatively related to adolescents' prosocial behavior. Reported negative expressivity in childhood was negatively related to boys' sympathy in childhood and positively related to girls' sympathy behavior in adolescence. The later relation remained significant when controlling for the stability of parental expressivity and sympathy, suggesting an emerging positive relation between the variables for girls.