The increasing popularity and widespread use of the Internet has made it an emerging venue for delivering health-related messages and interventions. The current study explored the potential for using social networking sites (SNS), specifically MySpace, to connect youth to sexual health services. Surveys and focus groups with youth aged 14–19 living in low-income communities in California revealed high levels of overall Internet access, frequent use of SNS, and experience in searching for health information online. However, disparities in frequency and location of Internet access by race/ethnicity, and hesitancy among some youth to join a clinic’s online social network, may affect the success of this new strategy in some populations. Interviews with clinic staff highlighted the successes and challenges of using MySpace as part of their outreach efforts. Staff described balancing the benefits of web-based outreach, including its low cost, wide reach, and teen friendliness, with its challenges, including overcoming technological barriers, ensuring teens’ safety from inappropriate contact, and remaining timely and relevant given the dynamic nature of the Internet. This study indicates that SNS and other technologies have strong potential for reaching diverse youth with critical health information when implemented as part of a comprehensive outreach strategy.