A sample of 187 African American adolescent females, who have been in outpatient psychiatric care, and their female caregivers participated in Growing into Responsible Leadership While Talking About Love and Kinship (GIRL TALK), a longitudinal study examining the individual and familial factors that contribute to HIV risk exposure in this population. The current study explored the effects of warm parenting, female caregiver relationship schemas, adolescent relationship schemas, communication about sexual risk-specific topics, style of communication (e.g. openness), and sexual behavior progression on adolescent risky sexual behavior. Analyses only included adolescent and caregiver self-report questionnaires from the baseline time point of data collection. Findings suggested that warm parenting style is important in increasing the number of risk-specific topics that are discussed between female caregivers and daughters. In addition, a greater number of sexual risk-specific topics discussed between mother and daughter is positively associated with a greater number of sexual risk-specific topics discussed between daughter and her partner. Regression analyses also indicated a significant mediation such that daughter-partner risk-specific communication mediated the relationship between mother-daughter risk-specific communication and adolescent risky sexual behavior. Finally, sexual behavior progression was found to have a significant negative association with overall adolescent risky sexual behavior, such that adolescents who engage in a greater number of pre-coital sexual behaviors before actually engaging in sexual intercourse also tend to engage in less HIV risk behaviors. Implications for prevention programs and future research are discussed.