Up in the Air is a fiendishly clever cinematic trick, which plays on but undercuts viewers’ expectations.
It begins by introducing the character of Ryan Bingham, a man who fires people for a living when companies are too scared to deal with the fallout of firing their own employees. George Clooney is perfectly cast as this smarmy but vaguely sinister cynic. At this beginning stage, the movie seems to be almost a cheerful riff on Fight Club, as, amidst snappy editing, Bingham gives a lecture on the unimportance of personal possessions, and has an interior monologue which finishes his sentences by thinking things he wouldn’t say to other people. He also has no real home, as he is constantly traveling for his job. The only difference between him and the Fight Club narrator is that he enjoys what he is doing.
But then, he meets Alex Goran, played by Vera Farmiga, who is similarly always on the road. They meet, hilariously, by comparing rewards cards, and discussing their attempts to joint the mile high club. As they begin a casual relationship, Bingham is called off the road because his company has decided to conduct its firings by video chat. This plan is spearheaded by Natalie Keener (Anna Kendrick), a young woman who manages to remain idealistic even as she works to streamline the firing process. Bingham is upset by not being able to travel anymore, so he convinces Keener to go on one final trip, in an effort to demonstrate how important it is to fire people in person.
As they travel, and meet with Goran on the way, it seems to be clear how the movie is going to unfold. Far from the Fight Club it seems to be referencing, this is going to be a classic Hollywood redemption story. The happy but heartless Bingham is going to reconcile with the family who he almost totally ignores, and continue his romance, eventually settling down with Goran, at the prompting of the younger and more idealistic Keener. And for a while, this is exactly what happens. Kendrick can’t help but radiate charm, which plays well against the smiling cynicism of Clooney and Farmiga, so the process is enjoyable, but events start to become very predictable.
After some lectures by Keener, Bingham invites Goran to his sister’s wedding, and, in a moment that could only happen in a movie, he makes sure the wedding actually happens, when the groom gets cold feet. Meanwhile, Goran meets the family and they approve of her. Then, some time after the wedding, after being apart from Goran  for a little while, Bingham decides to visit her. After landing in her home city of Chicago, yet another moment occurs that could only happen in a Hollywood movie. He rents a car, but it is revealed as he drives away that he has forgotten to show his “Hertz Gold Rewards Card” that he had been so obsessed with before he met the woman he would settle down with. The symbolism is heavy and boring. He drives up to Goran’s house, and I’m not positive, but I think there might actually be snow falling as he knocks on her door. And... she’s married.
At this moment everything changes. On his way home, he logs his ten millionth mile in the air. He had been obsessed with accomplishing this feat, but he no longer cares at all. All he wants is to settle down with Goran, but she will only have him on a casual basis.
When he arrives home, he’s called into the office, where it is revealed that a woman he and Keener fired has killed herself. Due to the fallout from this, Keener quits, and the online firing is suspended and he is sent back on the road. He writes a glowing reference letter for Keener to get a new job, but as he flies away his monologue reveals that he isn’t really happy with his solitude anymore. He has, in the cliched Hollywood way, grown a heart. But, instead of changing his life, it has just prevented him from enjoying it.