This four-year study with annual measurements investigated the longitudinal interplay between affective and cognitive empathy in adolescents and their mothers. We studied 1) whether the developmental order of empathy in adolescence progresses from affective to cognitive empathy, or vice versa; 2) whether mothers’ empathy predicts their children’s empathy development; 3) whether adolescent gender moderates such intergenerational transmission from mothers to adolescents; and 4) whether inter-respondent differences in empathy were more stable for affective or cognitive empathy, and for adolescents or for mothers. Results indicated that affective empathy positively predicted the development of cognitive empathy one year later, but not vice versa. Mothers’ greater cognitive empathy predicted increasing cognitive empathy over time in daughters, but not in sons. Inter-respondent differences were more stable for affective empathy than for cognitive empathy in adolescents. In mothers, both empathy dimensions were equally stable, and more stable than in adolescents. This study thereby suggests that the developmental order of empathy in adolescence progresses from affective to cognitive empathy, in contrast to prior experimental and theoretical work which has emphasized the reverse direction of effects. It further offers support for the intergenerational transmission of cognitive empathy over time. Together with the lower stability of cognitive empathy, these findings suggest that adolescence is a developmentally sensitive period for cognitive empathy.