The current study examines adolescents’ subjective experiences interacting with same-gender and other-gender friends, with a focus on interactions involving disclosure about personal problems. Participants were 510 youth (65% White or European American, 26% Black or African American) in seventh grade (n = 244; M = 13.01 years; 51% girls) and tenth grade (n = 266; M = 16.03 years; 52% girls). Adolescents completed an event-contingent sampling assessment to record interactions with same-gender and other-gender friends. Results indicated that middle adolescents were more likely to interact with other-gender friends than early adolescents. Girls were more likely to report problem disclosure interactions than boys; however, boys reported more positive subjective experiences in problem disclosure interactions with other-gender friends than did girls.