Music is kinda the only place where we’re allowed to be completely obsessed with our failures. Most of the time, we’re told to "move on" or "grind harder," but the minute a certain melody starts playing, you're right back in that 2014 Honda Civic, wondering why you let a perfectly good person walk out of your life. It’s a specific brand of grief. It isn’t the sharp, jagged pain of a fresh breakup; it’s the dull, persistent ache of a "what if." Songs about the one that got away have basically become their own genre because humans are statistically prone to rumination. We love to poke the bruise.
Honestly, we’ve all been there. You see an Instagram story of someone you haven't talked to in five years, and suddenly you’re spiraling. Is it the person you miss, or just the version of yourself you were when you were with them? Artists like Katy Perry, Taylor Swift, and Adele have made millions by answering that question with a resounding "both."
The Psychology of the "Almost" Relationship
Why do we do this to ourselves? Psychologists call it the Zeigarnik effect. It’s a fancy way of saying our brains hate unfinished business. When a relationship ends because of a blow-up fight, there’s a sense of closure, even if it’s messy. But when it ends because of "bad timing" or a move across the country, your brain stays stuck in a loop. You’re looking for a finale that never aired.
Music provides that missing ending. When you listen to something like "The One That Got Away" by Katy Perry, you’re not just hearing a pop song about June gloom and matching tattoos. You’re engaging in a collective ritual of regret. It’s cathartic. It lets you feel the weight of your choices without having to actually send that "I miss you" text that you’ll definitely regret by 9:00 AM tomorrow.
The Tracks That Actually Define This Feeling
If we’re being real, not every sad song fits the criteria. A "one that got away" track needs a specific mix of nostalgia and self-blame. It’s not about the person who cheated on you; it’s about the person you weren't ready for.
The All-Timer: "The One That Got Away" by Katy Perry
This is the gold standard for a reason. Perry ditches the candy-coated persona of the Teenage Dream era to talk about a relationship that felt like a lifetime but ended in a "used-to-be." The lyrics mention Radiohead and a June gloom, details that feel visceral. It’s a masterclass in the "could have been." She’s not mad at him; she’s frustrated with the universe and herself. It’s about the realization that in another life, you would have made it work. But in this life? You’re just a stranger with a lot of memories.
The Nuance of Taylor Swift’s "Back to December"
Most breakup songs are about how the other person messed up. Taylor flipped the script here. She’s the one who was cold. She’s the one who didn't give enough. That’s the core of the "one that got away" trope—the crushing weight of accountability. You realize, far too late, that you had something incredible and you simply didn't hold onto it tight enough. It’s a public apology set to a string arrangement, and it’s devastatingly effective because it’s so rare to hear a pop star admit they were the problem.
The Quiet Ache of "Someone Like You" by Adele
Adele didn't just write a song; she wrote a cultural event. The genius here isn't just the vocal performance. It's the setting. She’s showing up uninvited, not to cause a scene, but just to see if the person still remembers. It captures that terrifying moment when you realize the person you thought was "yours" has built a whole new life that doesn't include you. They have a wife. They’re happy. And you’re still standing there with your heart in your hands like a ghost.
Why Some "One That Got Away" Songs Fail
There’s a thin line between a timeless classic and a whiny track that doesn't land. The bad ones feel manipulative. They try to force the emotion with over-the-top production. The ones that actually rank and stay in the public consciousness are usually the ones that focus on the small, mundane details. A specific brand of coffee. A certain street corner. A song on the radio.
People don't relate to "I'm so sad." They relate to "I saw a car that looked like yours and my heart stopped for three seconds."
The Scientific Reality of Regret
In 2011, researchers Neal Roese and Amy Summerville conducted a study on regret. They found that romance is actually the number one source of regret for most people, outranking education, career, and even parenting. We are wired to obsess over our romantic "near-misses." This is why songs about the one that got away will never go out of style. As long as people make mistakes—which is forever—there will be a market for music that validates that specific type of loneliness.
It's also worth noting that we tend to romanticize the past. It’s called "rosy retrospection." We remember the late-night laughs but conveniently forget the three-hour arguments about whose turn it was to do the dishes. Music leans into this bias. It lets us keep the highlight reel playing while we ignore the bloopers.
The Cultural Shift: From Grief to Growth
Recently, the way we write these songs has changed. In the early 2000s, it was all about the tragedy. Now, there’s a bit more "it is what it is" energy. Look at Olivia Rodrigo’s "traitor" or even SZA’s work. There’s a sharper edge to it. It’s less about "I’ll wait for you forever" and more about "I’m haunted by this, but I’m still moving."
This shift reflects a more modern understanding of mental health and boundaries. We recognize that the "one that got away" might have actually been the "one you needed to lose" to become the person you are now. It doesn't make the song any less sad, but it adds a layer of complexity. You can miss someone and still be glad they’re gone. It’s a weird, human contradiction.
The Role of Social Media
Instagram and TikTok have fundamentally changed how we experience these songs. You can’t just wonder where someone is anymore. You know exactly where they are. You know what they had for brunch in Tulum. This constant digital proximity keeps the wound open. It makes the lyrics of a song written in 1995 feel even more relevant today. When Joni Mitchell sang about "A Case of You," she didn't have to deal with her ex's LinkedIn updates. We do.
How to Handle the "One That Got Away" Spiral
If you find yourself listening to these tracks on a loop, you’re basically doing emotional "exposure therapy." A little bit is fine. It helps you process. But too much can keep you stuck in a version of the past that doesn't even exist anymore.
Here is the truth: The "one that got away" is often an idealized version of a person. You aren't missing the actual human being; you’re missing the potential you saw in them. You’re missing the "you" that existed before life got complicated.
💡 You might also like: This Is Us Season 2 Episodes: What Really Happened to Jack Pearson
Actionable Next Steps
If a song has you spiraling about a past flame, try these three things to get your head back in the present:
- Audit the Memory: When a song triggers a "perfect" memory of an ex, force yourself to remember one time they really annoyed you or let you down. It breaks the "rosy retrospection" loop and grounds you in reality.
- Update Your Playlist: If your "On Repeat" is 90% heartbreak, intentionally add five high-tempo, lyrically aggressive songs. It sounds silly, but changing your physiological state through BPM (beats per minute) can actually shift your mood.
- The "Draft" Rule: If a song makes you want to reach out to them, write the message in your Notes app instead. Leave it there for 24 hours. Usually, by the next morning, the "song-induced" emotional peak has faded, and you’ll realize that sending it would have been a disaster.
The beauty of music is that it allows us to visit the past without having to live there. Listen to the song, feel the ache, and then turn the volume down and get back to your life. The person might have got away, but you’re still here. That’s what matters.