Music News

“Cornelia Street”

Album: Lover

Why it’s heartbreaking: This one might be the most obvious in the mix — fans have literally been making pilgrimages to Swift’s infamous West Village apartment to mourn — but “Cornelia Street” is straight up painful now that “Toe” is no longer. On this Lover fan favorite, the pop star vows to never again go near the tucked-away New York home she and Alwyn once shared if they broke up, because the pain of it all would be that catastrophic.

Saddest lyric: “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”

“Death By a Thousand Cuts”

Album: Lover

Why it’s heartbreaking: Swift once jokingly bragged about how “Death By a Thousand Cuts” proved she was still able to write exquisite breakup songs even while in a happy, healthy relationship (see: her Tiny Desk concert). But now, she probably relates to its piercing lyrics in real time, for the first time since she wrote them — which, if true, is such a cruel twist of fate.

Saddest lyric: “My heart, my hips, my body, my love / Trying to find a part of me that you didn’t touch / Gave up on me like I was a bad drug”

“Last Kiss”

Album: Speak Now

Why it’s heartbreaking: Yes, “Last Kiss” was written a long time before Swift ever met Alwyn. But the raw pain of one of her most brutal breakup songs seems fresh again; the hook “never thought we’d have a last kiss” is especially fitting for a love that, to outsiders, seemed like it would last a lifetime.

Saddest lyric: “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”

“Midnight Rain”

Album: Midnights

Why it’s heartbreaking: This Midnights track didn’t ring any alarm bells at the time of its release; fans generally assumed the clashing personalities described in the lyrics were written about an ex, not Alwyn, who was believed to still be her boyfriend at the time. Now, it seems plausible that “Midnight Rain” was actually an early warning of the reported differences that ultimately caused Swift and Alwyn’s breakup.

Swift has been open in the past about how the Favourite actor prefers a private, quiet, not-so-glamorous lifestyle. And in “Midnight Rain,” that’s the exact type of partner she describes needing to leave behind: “He wanted it comfortable, I wanted that pain / He wanted a bride, I was making my own name.”

Saddest lyric: “I guess sometimes we all get just what we wanted / And he never thinks of me, except when I’m on TV”

“Dancing With Our Hands Tied”

Album: Reputation

Why it’s heartbreaking: This anxiety-fueled track encapsulates a recurring theme on Reputation: fear that Swift’s hectic life would somehow cause her to lose her love. Actually, that’s a recurring theme throughout her latter discography — but more on that later.

No one knows for sure what truly caused the breakup, but it’s hard not to sympathize with Taylor upon discovering that this fear came true, at least to an extent.

Saddest lyric: “I loved you in spite of deep fears that the world would divide us / So, baby, can we dance / Oh, through an avalanche?”

“Lover”

Album: Lover

Why it’s heartbreaking: The title track of Swift’s mushy-gushiest album ever is one of the purest, most joyful love songs in her discography. In professing to have found her forever partner after years of getting her heart broken time and time again, “Lover” gave fans in similar boats hope that a soul mate was out there waiting for everyone — now, it doesn’t feel so certain.

Saddest lyric: “Can I go where you go? / Can we always be this close forever and ever?”

“Invisible String”

Album: Folklore

Why it’s heartbreaking: Throughout “Invisible String,” Swift seems to give vignetted snapshots of her fated relationship with Alwyn, from his childhood job at a yogurt shop to their three-year anniversary lakeside vacation. The motif of this folksy serenade is that she and her beau were destined from the very beginning by a metaphoric “thread of gold” that connected them through all their ups and downs.

To know that the thread was broken — or worse, never actually existed — is wildly depressing.

Saddest lyric: “A string that pulled me out of all the wrong arms right into that dive bar / Something wrapped all of my past mistakes in barbed wire / Chains around my demons, wool to brave the seasons / One single thread of gold tied me to you”

“The Great War”

Album: Midnights (3am Edition)

Why it’s heartbreaking: The message of this deluxe Midnights stunner is that Swift’s relationship went through a grueling, nearly fatal rough patch before coming out stronger on the other side. She sings of jealousy, trust issues and arguments that nearly made her lose the one thing that really mattered. But because they got through it, nothing would ever be able to separate them again.

Saddest lyric: “That was the night I nearly lost you / I really thought I lost you”

“Peace”

Album: Folklore

Why it’s heartbreaking: Again, we have Swift addressing her fear that the tumultuousness of her life might interfere with her ability to preserve her relationship. “If you’re gonna be in my life, there’s a certain amount that comes with it I can’t stop from happening,” she said of the meaning behind “Peace” in her Folklore: The Longpond Studio Sessions film. “This song was basically like, is it enough? Is the stuff that I can control enough to block out things that I can’t?”

Saddest lyric: “Give you the silence that only comes when two people understand each other / Family that I chose, now that I see your brother as my brother / Is it enough?”

“Champagne Problems”

Album: Evermore

Why it’s heartbreaking: Part of what makes the fictional breakup story in “Champagne Problems” so devastating is how Swift wrote the song with Alwyn, credited under the pseudonym William Bowery. Were they predicting their own split years before it went down without even knowing it? We’re not crying, you’re crying.

Saddest lyric: “One for the money, two for the show / I never was ready, so I watch you go”

“Sweet Nothing”

Album: Midnights

Why it’s heartbreaking: “Sweet Nothing” now feels like a premature response to the fears expressed on “Dancing With Our Hands Tied” and “Peace.” Also written with Alwyn, this simple lullaby seemed to say: yes, as long as we have each other, that’s enough.

Saddest lyric: “All that you ever wanted from me was nothing”

“You’re On Your Own, Kid”

Album: Midnights

Why it’s heartbreaking: Midnights’ Track 5 finds Swift realizing that no one is waiting at the end of the road for her, not even her partner — which is telling, given recent events. All this time she’s been alone, for better or for worse, even when she thought she had it all.

She doesn’t look back with regret, though. And at the end, she reminds us that we shouldn’t either: “Everything you lose is a step you take / So make the friendship bracelets / Take the moment and taste it / You’ve got no reason to be afraid.”

Saddest lyric: “I gave my blood, sweat, and tears for this / I hosted parties and starved my body / Like I’d be saved by a perfect kiss”

“White Horse (Taylor’s Version)”

Album: Fearless (Taylor’s Version)

Why it’s heartbreaking: A teenaged Swift used to prophesy that someday, she’d find her Prince Charming. After ten years, it seemed like she finally had.

Sigh.

Saddest lyric: “I’m gonna find someone someday who might actually treat me well”