The concept of the third space is a broad area of interest for educational researchers, particularly within art education. This realm is often tied closely to elements of popular culture, and may often enter subversive, transgressive, and inane territories. In the 21st century, teenagers are spending vast amounts of time online, engaging in the same informal types of play, socialization, learning, and art making as occur in real life (IRL). Because of these issues, some have responded by exploring the hybrid "third space" between formal and informal learning spaces, both on- and offline. The third space integrates concepts like playful pedagogy into learning, and it is typically seen as a productive co-mingling of teacher and student interests. However, this study traces the third space to its roots as a discourse of dissent and conflict, and examines the unique tensions that arise in this space and their implications for art education. This qualitative case study examines the researcher’s efforts to facilitate a third space for learning in the Digital Arts Workshop (DigArts). This workshop was designed as a third space that intended to facilitate a productive space for tech-savvy teens to meet, work on self-initiated projects, and forge a cooperative community of art makers. This report presents a survey of the digital visual culture of these teenagers, and discusses the various tensions that arise in the third space between teacher and student, formal and informal learning, offline and online.