This 4-year study examined longitudinal interplays between adolescents’ and mothers’ self-reported empathic concern (EC) and perspective taking (PT). We investigated (a) whether adolescents’ EC predicted rank-order change in their PT over time, or vice versa; (b) whether mothers’ empathy predicted relative increases in adolescents’ empathy; (c) whether adolescent gender moderated the over-time links from mothers’ to adolescents’ empathy; and (d) whether the rank-order stability of EC and PT over time differed within and between respondents. Adolescents’ EC positively predicted their PT over time, but not vice versa. Mothers’ PT positively predicted adolescent PT over time for girls, but not for boys. The rank-order stability of adolescents’ EC was greater than their PT. Maternal PT and EC were equally stable and were more stable than in adolescents. This study contributes the first empirical evidence that the developmental order of adolescents’ empathy runs from affective to cognitive empathy, in contrast to prior theoretical and experimental literature that has emphasized the reverse direction. It further provides the 1st longitudinal evidence of intergenerational empathy transmission. These findings support the notion that adolescence is a developmentally sensitive period for PT.