New digital technologies are highly responsive to many of the developmental needs of adolescents, including their need for intimate connection and social identity. This chapter explores adolescents' use of web-based sexual information, texting and "sexting," online dating sites, role-playing games, and sexually explicit media, and presents new data comparing the interpersonal and intrapersonal health outcomes among youth who engage in online sexual activities to those who do not. Despite the media-stoked concerns surrounding adolescents' participation in online sexual activities, the ubiquity of online activities and close overlap between online and offline activities indicate that this type of behavior should not be pathologized or used as a metric of problem behavior. The chapter concludes with implications for parents, educators, researchers, counselors, and health care providers, a call to challenge our deep discomfort around adolescent sexuality and to harness these technologies in ways that help promote growth and positive development.