You may have noticed that it’s been a little quiet around here lately. I have a habit of not forcing myself to write unless I feel a great surge of inspiration. I wouldn’t say that this is the best way to complete your next piece as a writer, as it’s a good rule of thumb to fight through these periods of “writer’s block” and just get something down (a rule that I am admittedly very bad at following).

My goal for the future is to break this habit. My goal for today is to tell you about the surge of inspiration that hit me on Monday while I was taking the train downtown. It involves George Clooney and a little film known as Up in the Air. Why did a movie from 2009 randomly pop in my head while I was on the light rail? No idea. This is one of the reasons that I liken films to old friends: you can go months or even years without coming across them, but one day they just appear again and you instantly reconnect with them.

Maybe part of the reason it was this particular film is that Up in the Air is all about connections: the ones we don’t make, the ones we do and wish we hadn’t, and the startling realization that life just isn’t the same without them.

In order to truly explore this, I am going to go in-depth with the plot details here. If you continue, you’ve already seen the movie or just don’t care about spoilers. Power to you.

Ryan Bingham fires people for a living. His company sends him around the country to help other companies who have trouble letting people go, or as he puts it, “Pussies who don’t have the balls to sack their own employees, and in some cases for good reason, because people do crazy shit when they get fired.” Some of that craziness includes cursing, storming out or even nonchalantly threatening to commit suicide. One former employee even follows through with that, although Ryan doesn’t learn of this until much later.

The point is that this occupation likely requires a certain amount of detachment from the person in that role, and no one is more detached from other people than Ryan. His philosophy and even some of his motivational speeches are centered around letting go of all the baggage in your life, and then moving on carefree without anyone or anything to weigh you down. This of course crosses over into his love life, and was there any better casting choice for a carefree, casual bachelor than George Clooney?

Most likely not. Clooney is so naturally charming, witty and so easily incorporates those traits into his character that you instantly wind up liking Ryan, even if you disagree with all of his lifestyle choices. Natalie Keener certainly does, as any ambitious young adult who dreams of having the perfect marriage would. She finds him childish, he thinks she’s naive and while a mutual respect does develop between the two while they’re out on the road together, there is always tension present. Ryan’s older sister is even more of a thorn his side. While he’s perfectly content with the isolation that his job affords him, she doesn’t understand why he insists on remaining so aloof from his family.

The only person who does fully understand and support his choices is Alex, a fellow frequent flyer whom he encounters one night in a hotel bar. They share an instant connection and a romance blossoms. The ground rules of said romance are made clear and things will go swimmingly so long as things remain casual. Of course, the more time that Ryan spends with her, and the more that Natalie needles him about not wanting to commit to Alex, the more he begins to question his philosophy. It may be the cruelest form of irony: here is someone who perfectly fits what he would want out of a relationship, only now he isn’t sure if that’s what he really wants.

Because of how abruptly and suddenly their romance ends, this is a good example of a film that will change for you upon your second viewing. On your first go-around, you take joy in seeing Ryan make an actual connection with someone, and then feel betrayed when it’s revealed that Alex is married with a family and sees Ryan as nothing more than an escape. Once you know the twist is coming, the film then confronts you with a difficult question: is Alex heartless for keeping her personal life a secret, or should Ryan have known that seeking an actual relationship with someone with the same philosophy as him was rather foolish? Probably a little bit of both.

What’s at stake here is not whether Ryan will end up happy with Alex, but whether he discovers value in a connection with another person. There are two scenes that cement this transformation for him. The first is when his younger sister’s fiance gets cold feet on the day of their wedding (a wonderful cameo from Danny McBride), and Ryan is tasked with bringing him away from the brink. “Life’s better with company. Everyone needs a co-pilot,” Ryan tells him, and there’s the ever subtle nod that Ryan is actually telling himself this. The second is when Ryan begins yet another one of his motivational speeches and finds himself at a loss for words. They elude him because he no longer finds any truth in them.

Ryan is in uncharted territory by the last scene. Will his job start to wear on him now that he isn’t so easily detached from others, and in a way has now been fired himself? Is his long pause at the destination board a metaphor for his uncertain future? Or is this just the start of a much more fulfilling journey in his life?

I love that Up in the Air lets you take what you will from its ending. Maybe it resonates with you, maybe it doesn’t, but I have a feeling that you’ll take something different each time you come back. Perhaps that’s why it bursts into my mind every once in awhile: it’s telling me that I have something new to discover about myself.