This study assessed early adolescents’ sexual communication with dating partners, parents, and best friends about six sexual health topics: condoms, birth control, sexually transmitted diseases (STDs), human immunodeficiency virus/acquired immunodeficiency syndrome (HIV/AIDS), pregnancy, and abstinence/waiting. Using a school-based sample of 603 youth (ages 12 to 15; 57% female; 46% Caucasian), we examined communication differences across demographic and developmental factors, tested whether communication with parents and best friends was associated with greater communication with partners, and examined associations between communication and condom use. More than half of participants had not discussed any sexual topics with their dating partners (54%), and many had not communicated with parents (29%) or best friends (25%). On average, communication was more frequent among adolescents who were female, African American, older, and sexually active, despite some variation in subgroups across partner, parent, and friend communication. Importantly, communication with parents and friends—and the interaction between parent and friend communication—was associated with increased communication with dating partners. Further, among sexually active youth, increased sexual communication with partners was associated with more frequent condom use. Results highlight the importance of understanding the broader family and peer context surrounding adolescent sexual decision making and suggest a possible need to tailor sexual communication interventions.