Walter Mitty’s Fantasy and Other Red Flags

I

I remember at some point in early 2014, maybe in January, I watched The Secret Life of Walter Mitty at the theater. I remember going there with B., a girl I was dating at the time. I remember she loved the movie; it was her third time watching it. I remember I hated it, and I talked about how it reminded me of every underachiever who dreams his moment of glory will suddenly come.

I know less than two weeks later B. and I stopped talking altogether.

What happened between us is a haze. The way I remember it, everything had to do with the movie, in some way, but it’s been too long, and I’ve forgotten most of the details.

Two things, however, I remember clearly. The first is the scene in The Secret Life of Walter Mitty where Ben Stiller skates down the highway in Iceland. The soundtrack, the editing, the colors, the movement, the freedom, and the visual of Walter finally taking risks and enjoying life. It’s been over a decade since the film came out, and that scene still randomly pops up in my mind.

The second memory from that time: After leaving the theater, B. said to me, “You remind me of Walter.” Her voice, her face, she clearly meant something was wrong.

Because of that, I avoided the film for years; it was tainted. For me, it was nothing more than a superficial flick about some version of seizing the day. In my mind, it was a phony take on finding beauty in both small and big moments of life. Even typing it now seems corny.

I associated people who liked it with that underdog mentality. The type of guy who thinks in just one single moment his life will turn around and thinks he doesn’t need consistency or discipline. ‘He daydreams just like me’, everyone does, that’s not special.

Recently, thinking about movies that could be considered red flags, the memory came back, so I decided to rewatch it and try to figure out what she meant.


II

In all honesty, apart from the skating scene, all I could remember from the film was a soapy sense of inspiring optimism.

The opening scene doesn’t paint a flattering picture of Walter (Ben Stiller) and, by extension, of me. Walter starts his story by trying to contact Cheryl (Kristen Wiig), a woman he works with, through a dating site. There’s a technical issue, so he calls customer service. The guy there tells him the problem is that his profile is empty. Nothing is interesting about him; he’s incomplete. It turns out that Walter hasn’t done anything noteworthy in his life.

Instead of living life, Walter spends most of his time daydreaming. Fantastical scenarios where he’s the hero, where he’s interesting and charming. In fact, he daydreams so much it becomes a problem; he zones out when people talk to him and he misses important moments.

As I would soon realize, I had that in common with Walter.


III

Walter works for Life magazine as it’s about to turn from print to digital. His job is to find the picture that will go on the final cover of the magazine, but the negative is missing. Walter must track down the photographer Sean O’Connell (Sean Penn) around the world and find the negative.

It is during one of his travels that Walter reaches Iceland. At one point, he must skate down the highway to catch Sean before he leaves on a plane and disappears forever.

I watched as Walter skated downhill, waiting for that rush of dopamine I had felt years ago, but it never came. It was nothing like I remembered it. It’s a good scene, don’t get me wrong; just not nearly as magnificent as I had it in my mind. It ends way too quickly, there are too many cuts and jumps, and the music is not that great.

I had to stop the film for a few seconds. ‘If I was wrong about this, What else could I have misremembered?’, I thought.

On the other hand, there are many amazing sequences I had completely forgotten. The best of all might be when Walter decides to travel to Greenland to look for Sean: the music as he walks past the covers of Life; the overhead shot of the plane as it takes off and lands; Ben Stiller’s subdued smile of pride and excitement and a bit of fear.

The Secret Life of Walter Mitty is full of great cinematic moments like this. Because of that, I’m glad I watched it again. For more than a decade, I laughed whenever someone mentioned they liked the movie. And I was wrong, it only took a second viewing to see that.

“You remind me of Walter”. What did B. mean by that? Walter was about to find the missing negative and I still didn’t know what she meant.

By the end, Walter’s completely changed. He has learned to see the beauty in each moment and live in it without distractions; he has stopped daydreaming because he’s too busy doing. In the two hours it took for Walter to feel good about himself, I was feeling terrible about myself. Cinematic parallelism.


IV

After rewatching the movie, I decided to see how B. was doing now. I looked her up on Instagram, ‘Just like Walter at the beginning of the movie’, I thought as I debated whether or not I should ask her what she had meant back in 2014.

Don’t worry, I didn’t. She probably didn’t even remember; it would be creepy and weird. Also, in a way, I knew.

I expected a lot more Waltermittiness, or something like it. From what I could see, she was living a normal life; a few adventurous places; but mostly a normal life. Nothing to suggest she lived the way the prophet Walter told her to. She didn’t become a fearless adventurer and neither did I.

It turns out, she was right, I was like Walter; I had spent ten years creating fantasies and scenarios in my head about what she had said. I created a fiction around Walter Mitty and the people who liked it, and I never contrasted it with the real thing. Like the skateboarding scene, what I remembered was completely different from what happened.

I know that’s not what she meant when she said it, but that’s what eventually happened. I turned The Secret Life of Walter Mitty into a red flag for the wrong reasons. The real red flag when it comes to movies is when someone spends more energy resenting it than actually trying to engage with it on a deeper level.

Walter Mitty didn’t deserve my disdain. It was just a movie, maybe a great one. And B., I only remember her now because of a comment I didn’t understand at the moment, and maybe that’s my red flag.

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Comments 12
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Keanen Tregaskis
Keanen Tregaskis
 · January 24, 2025
I love how you compared this movie to real-life experiences and how the time between seeing the movie has changed your perception of it. Great article!
1
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Jeroo Casco
Jeroo Casco
 · January 25, 2025
Wonderful movie
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Ishika Banerjee
Ishika Banerjee
 · January 25, 2025
Your article is so interesting to read. It's uncommon to go back to a movie you thought offended you because of a personal experience and realize years later that your hatred for it was just a projection of your own flaws. Thanks for sharing I had a lot of fun reading this.
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Bob Woolsey
Bob Woolsey
 · January 25, 2025
Beautiful article. I remember watching Walter Mitty and feeling like you did the first time you watched it. I didn't have anyone to provide me with the existential questioning though. Maybe I should revisit it.
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Lucas.
Lucas.
 · January 25, 2025
Great article, DC. I really loved how you drew examples from your own life to detail the article. I identified with a lot of what you said, like creating scenarios in my head for 10 years. A joy to read. Thanks for sharing
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