This qualitative teacher research study employed narrative inquiry in order to gain greater understanding of how secondary teachers and students made connections using digital online media. Interviews, focus groups, internet artifacts, and other demographic data were used in this interpretivist study. The teacher and student participants utilized a variety of digital media technologies to connect in the classroom and online. Teachers used internet, online video, mobile phones, and social media networks to support their classroom lessons and to engage students in the learning process beyond the time and space boundaries of school. Teachers felt online digital availability would increase student learning and engagement inside the classroom. Students' media use was more social and relationship-driven. Teacher-student relationships began in classrooms and then extended into digital spaces. Students conveyed curiosity and fear towards socializing with teachers in digital spaces, while teachers seemed uncomfortable with purely social online interactions with students. Both groups struggled to break the boundaries established around teachers' private and professional lives. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]