YOUmedia is a teen learning space in various libraries, museums, and afterschool spaces throughout the country. This Case Study focuses on the flagship in the Chicago Public Library’s downtown Harold Washington Library Center. YOUmedia is dedicated to the interests of young people, and supported by librarians and mentors with expertise in digital media production. There is also an online social network, iRemix, where young people can share their work and communicate with peers and mentors. YOUmedia exemplifies the principles of connected learning by welcoming young people to engage in casual social “hanging out” with friends, as well as offering workshops and mentoring in interest areas that stretch knowledge and expertise and the connection to academic achievement and career opportunities.