Office hours have been an important facet of student learning in higher education for decades. High school teachers attempt to incorporate the same individualized instruction opportunity for their students, but the constraints of the high school system make this a difficult reality. Furthermore, the explosion of online social media has redefined the student social landscape over the last decade. As a result, new research has started to explore these digital Web 2.0 resources as an alternative educational opportunity to foster student-teacher communication beyond the classroom. This study provides a review of the pertinent literature based on college Facebook studies, and survey data assessing the student based want and usefulness of digital office hours at a large diverse public high school in the United States. Results indicated that direct interaction with a teacher is the preferred method of receiving academic assistance thus highlighting the potential for Facebook and other Web 2.0 utilities to foster individualized learning in the digital world. This concludes with recommendations for implementing public (Facebook, Myspace etc.) or private (segregated social networks) social networking systems to facilitate new Web 2.0 communication avenues. Future research should consider these recommendations when employing digital office hours at the high school level to ensure learning can occur in a safe and secure digital distance environment.