Why, Exactly, Do We Have Such a Fascination with ‘The One That Got Away’?
Woman looking out the window and thinking about 'the one that got away'
Life is filled with forks in the road: where to live, what career to pursue, which person to spend a life with—and practically littered with all the roads not taken. We all make choices based in anticipation that it might change our lives for the better in some way. But what happens if that choice turns into regret—the one that got away?
“The one that got away” is a popular trope for a reason. It’s the very human temptation of the backward glance toward an alternate world that might have existed—where we got the job, where we married the person, where we made a different choice that carried us down a different road. It’s the what if of the life we could have had—an idea that bleeds through to color so many of the stories we love. From lost opportunities and second-chance romances to more extreme tropes like famous heists and escape artists, why are we collectively so fascinated by the things—and people—that got away?
I wrote a book called Enchanted Hill that features many of these elements. The loss of opportunities and first loves. Unsolved art heists and escaped prisoners. Regret and redemption. And along the way, I confronted the idea: what is the appeal of the one that got away? Why is there a certain sort of melancholy pleasure in wondering what might have been if we had simply made different choices?
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'The One That Got Away' Scenarios
Here are “the ones that got away” that seem to most capture our attention.
1. The lost love
This one dominates our cultural narratives, from Jay Gatsby to The Eras Tour. There’s something inherently romantic about wondering “what if,” perhaps no more than when we’re remembering a person we were once convinced was a soul mate. Songs and tomes love to ponder whether people are meant to be while looking back at relationships that had all the potential but no staying power. Perhaps that’s why we love a second-chance romance—this dreamy idea that the person was right, but the timing wasn’t.
2. The missed opportunity
This is the life-changing break that was so close and then slipped away. An audition or an interview. A job in another city or country. Something monumental that was just within reach, and then lost. Whether we were the one passed over or the one to turn it down, it was a prime opportunity close enough to taste—and some nights might be spent wondering what might have been.
3. The high-profile heist
“The one that got away” seems to fascinate us whenever it involves something precious that was once in hand and then gone—even if it has no real relation to our actual lives. For example: the unsolved Isabella Stewart Gardner museum art heist, which has spawned countless books, investigations, and a Netflix documentary. The Antwerp diamond heist. The robbery of the Mona Lisa and multiple iterations of Munch’s The Scream. Egyptian grave robberies. Even mysteries like the disappearance of Amelia Earheart. We are drawn to be curious about things that once seemed safe and secure, and then were suddenly gone.
4. The outmaneuver-er
There are plenty of stories where we are rooting for the criminal to get caught (see #3)—and plenty where we are rooting for them to get away. This is the alternate twist given to the trope of “the one that got away,” and one that has little sadness or regret involved. We see this twist in classic films like Ocean’s Eleven, Shawshank Redemption and The Italian Job. These stories indulge the fact that sometimes we like to turn the diamond on its side and let the light catch it in a new way. This is the fun side of “the one that got away”—indulging the trope not for melancholic regret but for a bit of escapist fun.
5. When “the one that got away” was us
Anyone who has ever been snubbed—be it romantically, professionally or otherwise—might be tempted to fantasize about being “the one that got away.” It’s the allure that eases the sting of fresh—or even not so fresh—rejection; the reassurance that it really was them and not you. Or perhaps we’ve had a chance to ruminate on a life twist that we’re grateful for. That person we’re glad we didn’t end up with because we found someone better for us, or the job we’re thankful we didn’t get because the company eventually was investigated for fraud. Sometimes we’re the ones who dodged the bullet, and “the one that got away” isn’t about regret, but a profound sense of gratitude.
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'The One That Got Away' Meaning: Why Are We So Fascinated by the Things and People That Got Away?
These are just a few of the many facets to “the one that got away,” and they continue to dominate much of our art, cultural, and personal thinking. But why?
Perhaps because there’s something deliciously tempting about losing ourselves in what might have been. Reflecting on “the one that got away” offers all kinds of escapism from our real lives. There’s something in us that knows this thinking is most often a fantasy—that we are looking at what might have been through rose-colored glasses. But even this fanciful reflection can be a helpful tool for real life. As philosopher and psychologist John Dewey said, “We do not learn from experience... we learn from reflecting on experience.” It’s an exercise in returning to the meaningful choices that made us the people we are today, for better or worse.
Lucille Ball famously quipped, “I'd rather regret the things I've done than regret the things I haven't done,” and there’s a reason for that. Psychologists recently did a study that said humans tend to regret the things we didn’t do more than the ones we did. Perhaps that’s because the paths we didn’t take are still open to the fantasy of our imagination. We don’t have to face the gritty realities that likely would have accompanied them—something that might help bring our focus back to the life we’re living now.
So as cultural expressions mine the depths of “the one that got away,” from perspectives of mourning, reflection, gratitude and escapism, what is it, really? A guilty pleasure? Healthy reflection? Harmless fantasy, or a waste of energy on what might have been?
Ultimately, our enduring fascination with “the one that got away” becomes its own fork in the road, offering two paths that diverge in different directions—because the best version of the backward glance is the one that, paradoxically, helps us most move forward.
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Randall Kahn
Emily Bain Murphy is the author of critically acclaimed books for adults and young adults. Her newest book is ENCHANTED HILL, an adult historical mystery where two people with a dark, shared past collide during a week of glittering 1930s parties at a lavish California mansion.
