Despite ongoing prevention efforts, young gay and bisexual males continue to engage in sexual behaviors that place them at disproportionately high risk for HIV infection. Parental monitoring and parent-child communication have been found to be associated with low-risk sexual behavior among heterosexual youth, but the role of family interactions for gay and bisexual male youth remains largely unexplored. To help address this gap, an exploratory study of recorded and coded interactions among 35 gay and bisexual youth and their parents was done to begin to identify which types of family interactions were associated with youth high-risk sexual behavior. Parent-son communication that was mutual and low in conflict was found to be most prevalent among youth with the fewest reported high-risk sexual behaviors. These preliminary findings, along with a case example, demonstrate how social workers can coach families to engage in productive and potentially influential interactions that reduce HIV-related sexual behaviors among young gay and bisexual males.