This study examines the 2009 film Up in the Air as a vehicle for personal and cultural reflection, focusing on how co-writer, producer, and director Jason Reitman crafted the film reflection, focusing on how co-writer, producer, and director Jason Reitman crafted the film to encourage dialogue concerning the complexity of contemporary life. To investigate this concept, this study explicates two strategies of Burke's comic frame--comic enactment and comic clash--that function to cultivate tension between compelling and incompatible perspectives. This irresolvable tension leads the audience to experience what Rassmussen and Downey call dialectical disorientation. Ultimately, this essay suggests that this type of instructive disorientation can presage a shift in orientation.