This study examined patterns of: (1) racial socialization messages in dyadic discussions between 111 African American mothers and adolescents (M age = 15.50) and (2) mothers’ positive emotions displayed during the discussion. Mothers gave more total racial socialization responses to a hypothetical dilemma involving potential mistreatment by a White teacher than a dilemma involving rude treatment by a White salesperson. Mothers displayed more advocacy on behalf of their adolescents in response to the teacher dilemma than to the salesperson dilemma. Mothers displayed consistent emotional support of adolescents’ problem solving across both dilemmas but lower warmth in response to the salesperson dilemma. The role of adolescent gender in mothers’ observed racial socialization responses is also discussed.