Teenagers are increasingly using video chat systems to communicate with others, however, little research has been conducted to explore how and why they use the technology. To better understand this design space, we present the results of a study of twenty teenagers and their use of video chat systems such as Skype, FaceTime, and Google Hangouts. Our results show that video chat plays an important role in helping teenagers socialize with their friends after school and on weekends where it allows them to see emotional reactions and participate in activities like shared homework sessions, show and tell, and performances over distance. Yet video chat is also used to engage in more private activities such as gossiping, flirting, and even the viewing of sexual acts. This presents an interesting design challenge of supporting teen use of video chat while mitigating privacy and parental concerns.