In this study, we considered the impact of mothers' willingness to disclose about distressing events and rule transgressions on their adolescent children's willingness to disclose about similar events, as well as adolescents' ability to cope and to show concern for others. Mothers and their 12‐ to 14‐year‐old children (N = 125) were asked to say how likely they would be to talk about moderately distressing concerns as well as minor rule transgressions. Adolescent positive coping skills were also assessed. Teachers (N = 92) rated the adolescents' prosocial behaviors in the classroom. Adolescents' disclosure about distressing events and positive coping mediated the relation between maternal disclosure about distressing events and adolescent prosocial behavior. Further, maternal disclosure alone about both distressing events and rule transgressions was related to adolescent prosocial behavior through positive coping. These results suggest that mothers' willingness to talk about their own negative experiences can help children cope better and, ultimately, to show greater empathy and concern for others.