Contemporary adolescents engage in online sexual communication and sexual and romantic partners seeking to meet their social and developmental needs. In doing so, adolescents are afforded new opportunities to discuss sexual health in quasi-anonymous and ostensibly private settings, explore their sexual interests and identities, and gain access to peers and potential partners beyond their physical spaces. However, online environments also introduce risks for adolescents that include stigma and rejection and forms of cyberdating violence such as harassment and unwanted sexual advances. This chapter reviews the current literature on the prevalence, patterns, benefits, and drawbacks experienced by adolescents who engage in online sexual communication and partner seeking. We also offer several recommendations for future research, interventions, and best practices. To improve adolescent health, parents, educators, and healthcare providers must first acknowledge that adolescents engage in online sexual communication and relationships. Second, they must assess the positive and negative impacts of their experiences in these online spaces. Finally, interventions and education that address the potential health, well-being, and developmental impacts of online sexual communication and relationships should be developed collaboratively with adolescents to ensure relevance to their lives.