
Despite their relatively young age, Adele and Taylor Swift have solidified their positions as enduring symbols of heartbreak music. With both artists releasing new tracks this month, my emotions are entirely at their mercy. I’ve previously advocated for embracing this sad girl autumn (don’t let the name fool you; anyone, regardless of age, gender, or emotional state, can be a sad girl), and now, it truly feels like ‘tis the damn season.
Today, Swift released Red (Taylor’s Version), a re-recording of her celebrated 2012 album with the same title. One of my biggest regrets is squandering so much of my teenage angst on disliking Taylor Swift instead of appreciating her artistry. My newfound admiration for her stems largely from my support for artists’ rights to their own music; this re-recording project is Swift’s response to the sale of the masters for her first six studio albums.
On the power ballad front, Adele’s latest release, “Easy on Me,” is part of 30, her first album in six years. Adele shared that the upcoming album delves into “the most turbulent period” of her life. (Since her last album, 25, she has experienced both marriage and divorce).
But which of these queens of the perfectly crafted breakup anthem reigns supreme in our shattered hearts? Why choose? Simply blend the best of both. When it comes to the ideal breakup song, everyone needs something different depending on their emotional stage—catharsis, nostalgia, longing, regret, or any of the swirling feelings that accompany the end of a relationship. (I believe any song can be a breakup song if you’re sad enough.) This playlist covers all the emotional bases.
Taylor: “Last Kiss”
So I’ll watch your life in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe / And I’ll keep up with our old friends just to ask them how you are / Hope it’s nice where you are.
Navigating the aftermath of a breakup can be as complex as processing grief. “Last Kiss” beautifully encapsulates the desire to hold onto cherished memories that are slipping away. In a since-deleted post on her website, Taylor described it best:
The song ‘Last Kiss’ is like a letter to someone. You express all these desperate, hopeless emotions that follow a breakup. During a breakup, you experience a whirlwind of feelings—anger, confusion, frustration, and ultimately, profound sadness. The sadness of losing not just the person, but also the memories and the future you envisioned. There are moments of clarity where you admit to yourself how much you miss it all. I wrote this song during one of those moments.
When to listen: When you’re still processing the breakup and clinging to every vivid detail of what you’ve lost.
Adele: “Someone Like You”
Never mind, I’ll find someone like you / I wish nothing but the best for you, too / ‘Don’t forget me,’ I beg / I remember you said / ‘Sometimes it lasts in love, but sometimes it hurts instead.’
This track is destined to be remembered as one of the most iconic breakup songs of its era. It encapsulates everything: emotional release, deep reflection, vivid storytelling, raw pain, and a sense of maturity. Explaining why “Someone Like You” is the ultimate breakup anthem feels as obvious as explaining why the sky is blue or why cereal belongs in the bowl before milk.
When to listen: When you’re still drowning in heartbreak but are starting to convince yourself it’s time to move forward.
Taylor: “champagne problems”
Because I dropped your hand while dancing / Left you out there standing / Crestfallen on the landing / Champagne problems
At its core, this song narrates the tale of a failed engagement, with Swift being the one who ends it. The term “champagne problems” is her way of downplaying the situation, yet the song beautifully captures the feeling of knowing your breakup isn’t catastrophic, even though certain aspects still feel devastating to you or someone you love.
When to listen: When you were the one who ended things, but you’re still justified in feeling a deep sense of loss.
Adele: “When We Were Young”
“But if by chance you’re here alone / Can I have a moment? / Before I go? / ‘Cause I’ve been by myself all night long / Hoping you’re someone I used to know.”
Is there anything more nostalgic than this? A recurring theme in this list is my conviction that breakup songs are, above all, about reminiscing. Adele’s unparalleled talent for conveying sorrow makes you feel as though you’re watching your own life unfold like a cinematic masterpiece.
When to listen: When you need to idealize the past.
Taylor: “Cornelia Street”
I hope I never lose you, hope it never ends / I’d never walk Cornelia Street again / That’s the kind of heartbreak time could never mend / I’d never walk Cornelia Street again
This track is from Lover, an album that often ranks lower in Swift’s discography. However, the live renditions of “Cornelia Street” stand out, likely because the pop elements are replaced with raw vulnerability. Plus, I’m a fan of songs that name-drop specific people and places. (In a future piece, I’ll explore my theory that all songs should be named after streets or beautiful women, and nothing else.)
When to listen: When a particular location triggers an overwhelming wave of nostalgia.
Adele: “Chasing Pavements”
Should I give up? / Or should I just keep chasing pavements? / Even if it leads nowhere / Or would it be a waste?
This was one of the first songs that showcased Adele’s immense talent. We’ve all reached a point in our romantic journeys where it feels like nothing will ever work out. And if you haven’t experienced that, I’m definitely not bitter or jealous of your love life.
When to listen: When love feels like a myth, and you’re exhausted by all the dead ends.
Taylor: “White Horse”
I was a dreamer before you went and let me down / Now it’s too late for you / And your white horse ... ‘Cause I’m not your princess, this ain’t a fairytale / I’m gonna find someone someday who might actually treat me well.
This song brought back memories of Swift’s earlier, more innocent and “country” sound, which aligns perfectly with the track’s theme of growing up. “White Horse” captures the moment you realize your love life isn’t a fairy tale. Yet, the lyrics don’t portray Swift as naive or overly idealistic. Instead, it’s the perfect anthem for acknowledging that even if life doesn’t resemble the movies, you’ll still be alright.
When to listen: When you’re almost over a relationship but still grieving the lost hopes you once had.
Adele: “Hello”
Hello from the outside / At least I can say that I’ve tried / To tell you I’m sorry for breaking your heart / But it don’t matter, it clearly doesn’t tear you apart anymore.
This song is a must-listen during Thanksgiving (if you’re unaware of the reference, check out this 2015 SNL sketch). I’m not overstating when I say the chorus has a healing power that can mend emotional wounds.
When to listen: When you’re tempted to call your ex. Resist the urge! Instead, belt out “Hello” in your car like no one’s listening.
Taylor: “Back to December”
Maybe this is wishful thinking / Probably mindless dreaming / But if we loved again, I swear I’d love you right ... I’d go back in time and change it but I can’t / So if the chain is on your door I understand.
Another nostalgic choice, “Back to December” shines for its exploration of regret. It’s tough to admit when you’re the one who caused pain to someone you supposedly cared about. This song captures the longing to turn back time and fix mistakes (even if you no longer want to be with that person).
When to listen: When you need to process your remorse over how things ended.
Adele: “Don’t You Remember”
When was the last time you thought of me? / Or have you completely erased me from your memory? / I often think about where I went wrong / The more I do, the less I know.
Few experiences are as bewildering and painful as realizing someone has fallen out of love with you. This slow fade can feel worse than cheating or arguments because it’s hard to identify where things went wrong. Adele, why must you hurt us so? Why must you craft the perfect anthem for unrequited love?
When to listen: When you’re still grappling with the confusion and pain of being rejected or, worse, simply forgotten.
Taylor: “We Are Never Ever Getting Back Together”
I used to think that we were forever ever, ever / And I used to say, “never say never...”
This is the only upbeat track on this list, as breakup songs are typically about wallowing. I included it because I imagine singing it not as a bold declaration, but as a sobering realization. Picture it: “Wow...I’m never ever getting back with that person, am I?” There—I turned the happy song sad!
When to listen: When you need to remind yourself why you’re never going to reply to their text. Ever.
Adele: “Easy on Me”
I had good intentions / And the highest hopes / But I know right now / That probably doesn’t even show.
While soothing to the ears, this track is anything but gentle on your emotions. I might stir some controversy by saying this isn’t my favorite Adele song, but I can still admire the depth of heartbreak woven into its serene, soulful tones. The maturity Adele displays here has me eagerly anticipating her upcoming album, set to release in just a week.
When to listen: When you’re feeling introspective, older, and wiser.
Taylor: “All Too Well” (10-Minute Version)
And you call me up again just to break me like a promise / So casually cruel in the name of being honest / I’m a crumpled up piece of paper lying here / ‘Cause I remember it all, all, all / Too well.
I’ve reserved “All Too Well” for the end because, if scientists were to analyze it, they’d undoubtedly declare it the definitive breakup anthem. Taylor Swift has often mentioned that she could have extended this song to ten minutes during its creation. Now, those ten magnificent minutes are here. Listen, immerse yourself, and prepare your voice for the short film premiering tonight. When to listen: Honestly, when shouldn’t you listen?
