The film opens with various bird’s eye view shots of America—what protagonist Ryan Bingham (played by George Clooney) sees from his seat in the airplane. Up in the air is where he spends 320 days of his year, traveling from state to state as a corporate downsizing expert. Ryan chases frequent flyer points for the sole sake of earning them, and on one trip, meets a female version of himself in the form of Alex Goran (played by Vera Farmiga). They have a one-night stand and end up making dates in different states for their subsequent rendezvous.
Then appears another lady in his life, in the form of a young upstart Natalie Keener (played by Anna Kendrick). While Ryan gives motivational speeches on how to relieve oneself of emotional burdens, Natalie dreams about getting married and having children.
When Natalie comes up with a brilliant video-conferencing method to cut costs for the company, Ryan finds his purpose for existence threatened. Ironically, he is tasked with taking her along on his trips to show her the ropes. What follows is an amusing demonstration by Ryan on how to pack light and get through the airport security in the shortest time available. Clooney carries his witty lines with an ease that is subtle yet hilarious.
Ryan and Natalie both start to be affected by each other’s opposite values as they invariably come into contact with the more personal aspects of each other’s lives. Eventually, as Ryan begins to open up to the possibility of putting down roots, his relationship with Alex also takes on a twist. Although a predictable twist, it nevertheless provokes the viewer’s emotional response. It is then that the viewer realizes how quietly effective this film has been in its storytelling. Without much aplomb, it reels its viewers into participating in Ryan’s life journey.