Despite prior research indicating that parents and adolescents perceive conversations about the adolescent’s strengths and weaknesses to be important, information about these conversations and how they are related to other facets of the parent-adolescent relationship is limited. In a sample of 171 parent-adolescent dyads (adolescents were 14-17 years old), we conducted an initial exploratory study on the frequencies of parent-adolescent discussions about strengths and weaknesses. Within-dyad reports were correlated; however, parents reported higher frequencies of strengths-based communication and lower frequencies of weakness-based communication than adolescents. We also found differences in frequencies of weakness-based communication by socio-demographic variables. Spearman’s rank correlations and mixed-effects regression models suggested that the frequency of communication about strengths, but not the frequency of weaknesses, was associated with parent-adolescent general communication, adolescent disclosure, and relationship quality. These results help shed much needed light on an understudied topic of importance to adolescents and parents.