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*Spoilers Ahead*
The film never specifies which life style is better and it's good that it doesn't, that comes down entirely to the viewers perspective, whether you'd prefer a life of travelling or wish to settle down, there's not a wrong choice, what's important is that you at least experience the other and don't trap yourself into a rut, because eventually life will disrupt your rut for you. This is where Ryan comes in, his job is to fire people, to disrupt their rut, whenever he fires someone, they usually use their lifestyle as a defence mechanism, saying how they've worked for this company for X amount of years, that they have a family, a rut. In one scene, Ryan and Natalie fire Bob (JK Simmons) and Ryan helps him with alternative options, pointing out his potential as a culinary chef and giving him a new option for a career path and changing his current lifestyle. In another scene, Ryan has to convince his future brother-in-law Jim (Danny McBride) to go through with his wedding and stick to the life he's got, both cases he explains that they'd be better off in these directions, Bob to try a new lifestyle, Jim to stick to the one he's already got planned, because changing your rut may not be the answer, sometimes your rut is what's right for you, as long as you've tried both and you know for sure.
Alex (Vera Farmiga) is Ryan's friend, fellow frequent traveller and fuck buddy whenever the two travel to the same location is arguably the worst character in the film from a realistic stand point. After Ryan decides he's willing to try the settled down life, he goes to Alex, only to find that she has already being settled down and has a husband and children and has been cheating on them with Ryan. In reality this would make her the scum of the Earth, because she cheated on her husband, repeatedly. But in the context of the film and with this interpretation, she's the most well rounded and the only one who doesn't have to question her life choices because she does experiment outside of her rut and try new opportunities, in other words, she's having her cake and eating it too (Never understood the wording of that phrase).
If Up In The Air has anything definitive to say, it's this, you will never truly be settled, you can find a life you're happy with, or a life you're unhappy with, regardless, eventually something will come along to disrupt that for you. But if you want a happy ending then you better make the change happen yourself, rather than wait until life does it for you.
-Danny
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