The Best Taylor Swift Songs About Each Of Her Exes, Ranked
Taylor Swift doesn't like to talk about her personal life. But she certainly does like to sing about it. Of course, anyone who hasn't been living under a rock since "1989" will know that the singer has a history of penning lyrics about her experience with love, sometimes even dishing out relationship advice in her tracks. Like many other writers, Swift is inspired by her own real-life experiences. "I don't talk about my personal life in great detail. I write about it in my songs, and I feel like you can share enough about your life in your music to let people know what you're going through," she admitted during a Glamour interview in 2012.
Though the songwriter has had to clapback several times against those who criticize her choice to write about her past relationships (men, after all, do the same thing), many would argue it's a touchstone of her songwriting. Her ability to translate her memories into music has given us countless songs about heartache, being madly in love, wondering where she stands with a romantic interest, and, never ever wanting to see an ex ever again (like, ever).
Of course, when it comes to those songs about her high-profile exes (a few of whom have spoken out about her too), some are certainly more memorable than others. So we took it upon ourselves to celebrate our often lovestruck queen with a compilation of the best Swift songs that are allegedly about each of her exes.
Matty Healy: The Tortured Poets Department
We know, Taylor Swift's romance with The 1975 singer Matty Healy isn't exactly the most revered of her past relationships by Swifties, but we have solid reasoning for including the title track from "The Tortured Poets Department" album. The 2024 track is so classic Swift with its second-person POV that reminisces on the whirlwind of being part of a messy love affair, which you know deep down has no future, despite how fun it is in the moment.
Sure, lyrically, there are a few more questionable lines ("You smokеd, then ate seven bars of chocolate/We declared Charlie Puth should be a bigger artist," we're looking at you). But the way Swift brings us into her personal life and thoughts on this song has to be commended. Not to mention, the simpler, relatable lyrics actually make the song more approachable and real. She sings about having a partner who is in self-sabotage mode that she can't help but resist because of their 'golden retriever' demeanor. She jokes repeatedly in the chorus about how she and this person are both "modern idiots."
We admire the way she gets super vulnerable about how she felt about this guy (even though she may have since changed her mind), recalling at one point in the song, "At dinner, you take my ring off my middle finger and put it on the one people put wedding rings on/And that's the closest I've come to my heart exploding." Although she doesn't explicitly name Healy on the track, the lyrics make numerous references to the 1975 singer's behavior, as well as his penchant for typewriters. We have to give Swift credit for cleverness there.
Joe Alwyn: Lover
It's fair to say Swifties have a bit of a love/hate relationship with "Lover" now that Taylor Swift and Joe Alwyn have gone their separate ways. Sure, not many people like to look back on the love songs they wrote about the exes with fondness, but it's impossible to not appreciate how beautifully this chapter of Swift's life is captured by this love song. The mid-tempo tune sounds like it was made to be played at weddings; since its 2019 release, many people have taken instrumental versions to their nuptials.
Although Alwyn and Swift would go on to break up in April 2023 after a six-year relationship, "Lover" is a beautiful tribute to the pair's once thriving romance. The verses paint images of the two living a life of complacent domesticity; letting friends sleepover and leaving the Christmas lights up 'til January. Swift herself has admitted that the song's lyrics are particularly poignant for her because it was a departure from her usual relationship writing, which focused on being done wrong. This was an authentic love song. She sings about being in love with someone for three summers, but wanting them all — a wistful plea for lifelong matrimony. Miss Americana revealed during her 2019 NPR "Tiny Desk Concert" that she loves the line, "With every guitar string scar in my hand, I take this magnetic force of a man to be my lover." She explained, "[It's] really special to me because I've spent quite a bit of time writing break-up songs." Although things didn't last, we have to thank Alwyn for being the likely muse who inspired this unforgettable tune.
John Mayer: Dear John
"Dear John" may be a bit on-the-nose for titles, but as far as songs about ex boyfriends go, this may take the cake as one of her most memorable. The tune is widely believed to be about Swift's romance with musician John Mayer, who was 12 years her senior when they dated. This is in part due to the many lyric references to an age gap romance, as well as the fact that the guitar stylings used on the song sound suspiciously like Mayer's hit tune, "Gravity."
But aside from those clever details, what makes this "Speak Now," track a standout in her "songs about exes" catalogue is how it shows a shift in Swift's relationship writing. The lyrics show her expressing not only sadness, but regret over this relationship, as she realizes this person didn't have the same intentions she did. She doesn't hold back in calling him out directly. "Dear John, I see it all now that you're gone/Don't you think I was too young to be messed with?/The girl in the dress, cried the whole way home/I should've known," she sings on the chorus. This outpouring of feelings reads like something coming straight out her diary. Yet despite the specificity of the situation, this song belongs in the top 3 because it speaks to something familiar for anyone who has ever dated someone that took advantage of their naivety. Swift was learning a lot about life and hinted at the fact she'd done a lot of growing up and self-reflection after her dalliance with the musician.
Harry Styles: Is It Over Now?
Okay, we'll admit, we were torn between "Is It Over Now?" and "Style" when it came to songs about Harry Styles, but the former just pipped the 2014 single from "1989" to the post. Though "Style" offers a brief glimpse into the struggles of having to sneak around during a high-profile relationship (which fans affectionally have dubbed 'Haylor'), "Is It Over Now?" breaks open the window and tells us exactly what caused said relationship to fall apart.
On "Is It Over Now?", Swift looks back on a relationship with an ex and wonders where it all went wrong. It starts out with a calmer beat as she asks the guy when he knew their relationship was over. But the music quickly starts to match her more frantic and desperate mood as it builds into a somewhat frenzied crescendo, culminating in Swift making her confusion (and frustration) over this guy clear as things start to break down further. "Oh, Lord, I think about/Jumping off of very tall somethings/Just to see you come running/And say the one thing I've been wanting/But no," she sings. Even if the fantasy seems intense, many can likely relate to feeling like you need to be pushed to the brink of doing something dramatic just to see if that other person actually cares. The song also gathers pace while she also sings about a freak accident in the snow (Swift and Styles famously had an accident on a snow mobile), and we adore the way she goes beyond words to convey how she was feeling.
Jake Gyllenhaal: All Too Wel
Often hailed as one of her very best songs, "All Too Well" has gone down in Swiftlore as one of her most memorable tracks about an old flame, particularly the 10-minute version included on "Red (Taylor's Version)." But why is it so good? Because it's so vulnerable and the story is so well told. Swift quite literally pulls us into the setting of her and this ex during one autumn, noting everything from minute details about the weather, to the specific, recalled conversations she had with this ex's mom. It all feels so real, like you're right there experiencing this romance go sour with her. And, as Swifties will know, there's that whole deal with the notorious scarf mentioned in the lyrics too, which just makes the song all the more iconic.
She continues to hit us where it hurts with evocative lyrics like: "And maybe we got lost in translation/Maybe I asked for too much/But maybe this thing was a masterpiece 'til you tore it all up/Running scared, I was there/I remember it all too well." They're painful because they can be applied to so many romances that start off strong but die fast. It creates a feeling deeper than heartbreak; it's betrayal. Swift has even revealed that the track contains one of her favorite lyrics from "Red," while opening up about what inspired her to write it. "I was going through a really hard time then, and my band joined in playing, and one of the first things that I came up with, just, like, spat out, was 'And you call me up again just to break me like a promise, so casually cruel in the name of being honest,'" she told Popdust in 2012.