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The transition to middle school is a challenging time in adolescent development. Adolescents often approach their parents for guidance, yet our knowledge of effective parent-adolescent interactions remains limited. This study’s aim was to investigate how parents discuss difficult topics with their adolescents and how adolescents respond to and reflect on their parents’ strategies. Three triads (fathers, mothers, adolescents) participated in observations of conversations about difficult topics and fathers and adolescents were interviewed. We conducted within-case analyses to compare adolescents’ conversations with fathers to those with mothers, informed by interview data. We conducted cross-case analyses to compare four conversational strategies: validation, self-disclosure, vulnerability, dominance. Results may provide guidance for parents and counselors to improve parent-adolescent communication.