Everything Taylor Swift Has Said About Her Relationship Breakups

We've been totally in love with Taylor Swift's stunning transformation for years. We've watched her blossom in the spotlight, going from a young country starlet to the undisputed queen of pop music, selling out arenas across the globe. However, it hasn't always been an easy road for the hitmaker when it comes to her personal life. 

Arguably, Swift's love life has become a key part of her brand, as fans can't wait to see her detail the breakups through her slew of endless hits, from "All Too Well" to "So Long, London." The singer prefers to get it all out through the medium of song when spilling the beans about her exes, and we're more than here for it. 

However, there are times when she lets a little bit extra slip, whether that's in an interview, a documentary, or reflecting back on a certain situation when performing. She certainly has a lot of material to reference, and when you've dated some of the biggest names in showbiz, the interest never wanes.

When we look back at Taylor Swift and Taylor Lautner's relationship, it's hard not to crack a smile. The year 2009 was a truly magical time. Swift had well and truly arrived and had won Video of the Year at the MTV VMAs only for Kanye West to storm the stage, and Lautner was at the peak of his popularity as part of the uber-successful "Twilight" franchise. It seemed only natural that the pair would strike up a romance after meeting on the set of "Valentine's Day", but just like many of the singer's romances from this period, it didn't end well — though it wasn't down to Lautner. In this case, Swift was the one to do all the heartbreaking. 

Despite taking their tryst public and attending a hockey game as well as dinner together, it all came crashing down quicker than you can say "Teardrops on my Guitar." By December 2009, it was all over, but fans would get the lowdown in the "Speak Now" track "Back to December," which was released the following year. While Swift may have never confirmed who the song is about, it's widely believed to be about Lautner. With lyrics like, "Because the last time you saw me is still burned in the back of your mind, you gave me roses, and I left them there to die," it's not hard to see why. Swift later told E! News, "The person I wrote this song about deserves this [song]. This is about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him ... This is a song full of words I would say to him."

This boy's not a one-hit wonder. There are a few Taylor Swift songs everyone thinks are about John Mayer, but "Dear John" may be the most obvious in terms of signposting. For a start, his name is literally in the title, and Mayer is a notorious womanizer. The musicians first became involved when they collaborated on Mayer's song, "Half of My Heart," in 2009, which they performed together at the Jingle Ball that year (pictured above). At the time, Swift was 19 and Mayer was 32, making this an eyebrow-raising union at best. The songstress took aim at the age gap in her seemingly scathing lyrical review of the relationship in "Dear John."

"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," she sings on the track. "Dear John, I see it all now. It was wrong. Don't you think nineteen's too young, to be played by your dark, twisted games when I loved you so?" It was the ultimate teen angst breakup song, and we're still here for it. Mayer, however, felt it was a little too pointed. "I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that," he told Rolling Stone in 2012. "It was a really lousy thing for her to do."

It's no secret that Taylor Swift is among the most famous women Harry Styles has ever dated. Swift, who has a penchant for dating men from the other side of the pond, and Styles, got the gossip mill turning after they met at the Kids' Choice Awards in 2012, when Styles performed with his band, One Direction. Their paths crossed again when they both took to the stage at the MTV VMAs later that year, and in December, they were papped taking in the chilly New York air. The young stars lived it up during their time together, enjoying a trip to the Caribbean, but it's tough to keep a relationship together when you're both on the brink of megastardom. Naturally, Swift gave fans some insight into what went down when she released "Out of the Woods," a track featured on her album, "1989." Though she may have never explicitly said it was about Styles, fans didn't need much convincing.

In 2015, Swift celebrated the album turning a year old and introduced an acoustic version of the number in a video, explaining it was about a difficult relationship. "The number one feeling I felt in the whole relationship was anxiety," she said in the video (via the BBC). "Because it felt very fragile, it felt very tentative. And it always felt like, 'OK, what's the next road block? What's the next thing that's going to deter this? How long do we have before this turns into just an awful mess and we break up? Is it a month? Is it three days?'"

It's sort of magical when two musical powerhouses get together. In 2015, Taylor Swift hard-launched her relationship with Scottish hitmaker Calvin Harris on Instagram, going on to post a slew of photographs of the pair living it up throughout the summer with Swift's friends. As far as social media was concerned, it was a match made in heaven, with Swift and Harris sharing photographs of their beach getaway to celebrate their one-year anniversary together, and Swift even praising her beau in a Vogue interview. And then, just like that, everything came crashing down. Harris confirmed the split on Twitter (now X). "The only truth here is that a relationship came to an end & what remains is a huge amount of love and respect," the DJ wrote in a since-deleted tweet (per The Hollywood Reporter).

For her part, Swift said all she needed to say by retweeting Harris' statement. However, it didn't stay quite that amicable. Harris lashed out at his ex via Twitter in June 2016 amid speculation she was nearly wholly responsible for their shared work, "This Is What You Came For." In a string of since-deleted tweets (via People), Harris wrote, "Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad at this stage, though ... I figure if you're happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do. I know you're off tour, and you need someone new to try and bury like Katy, ETC, but I'm not that guy, sorry. I won't allow it." For the record, Calvin Harris wishes he didn't snap at Taylor Swift on Twitter after their messy breakup.

We can't deny it: this one stings. Out of all the men Taylor Swift has been romantically connected to, we had high hopes that Tom Hiddleston might have been the fairytale ending. Sure, we can be thankful now that all roads led to Travis Kelce, but in 2016, the dashing British actor seemed like the ideal wholesome gentleman to usher Swift into her post-Calvin Harris era. It started out so well, with the pair photographed celebrating the 4th of July. Hiddleston even famously rocked a white tank top with "I [love-heart] T.S." emblazoned across it. How much more serious can you get? However, the summer romance wasn't meant to last, and HiddleSwift was a thing of the past by the time Fall rolled around. Both have remained silent on the details surrounding the split ... as long as you don't count "Getaway Car." 

The catchy track is featured on Swift's 2017 album, "Reputation," and in it, Swift details the start and demise of a relationship that was doomed from the start. She croons, "It was the best of times, the worst of crimes, I struck a match and blew your mind. But I didn't mean it, and you didn't see it. The ties were black, the lies were white, in shades of gray in candlelight, I wanted to leave him, I needed a reason." Considering that Swift and Hiddleston met at everyone's favorite swanky event, the Met Gala, it's not a stretch for fans to connect the dots. Other damning lyrics include, "I knew it from the first Old Fashioned, we were cursed. We never had a shotgun shot in the dark." 

We may hate that Taylor Swift ever had the need to re-record her albums after that messy situation with Scooter Braun, but it didn't exactly suck, either. We got some gems from the whole process, including the 10-minute version of "All Too Well", an angsty ballad originally released on Swift's "Red" album in 2012. From the get-go, fans have been certain that the pointed track is about Swift's relationship with dreamy A-list actor, Jake Gyllenhaal, who she briefly dated prior to the album's release. In the original, Swift sings about the early days of a seemingly perfect relationship, before lamenting, "And I know it's long gone, and there was nothing else I could do, and I forget about you long enough to forget why I needed to."

The 10-minute version doubled down and twisted the knife with lyrics like, "They say all's well that ends well, but I'm in a new hell every time you double-cross my mind. You said if we had been closer in age, maybe it would have been fine, and that made me want to die." Talking about the new cut of the song on "The Tonight Show Starring Jimmy Fallon" in 2021, the hitmaker explained that this re-released version was actually the original cut of the song before it was edited down. "I showed up for rehearsals and I just was really upset," she explained. "I started ad-libbing what I was going through and what I was feeling."

There's no denying that Taylor Swift can write a heartbreaking song better than most. She has a song for every season, be it love, lust, or the devastation that comes with an ill-fated romance. In 2024, she released a surprise album, "The Tortured Poets Department," and with it, a song titled "So Long, London." The sweet ballad sees Swift sing the lyrics, "I saw in my mind fairy lights through the mist. I kept calm and carried the weight of the rift. Pulled him in tighter each time he was driftin' away. My spine split from carrying us up the hill." The song just ramps up from there, with an emotional Swift singing, "And I'm p****d off you let me give you all that youth for free. You swore that you loved me, but where were the clues? I died on the altar waitin' for the proof."

It was a sad swan song to a long-term love that was the catalyst for one of Swift's lighter albums, "Lover," and paints the picture of a couple ultimately torn apart by growing dissonance. As of publication, Swift hasn't publicly spoken about her relationship with Alwyn other than in her lyrics — she's been far too busy focusing on her endgame, Travis Kelce. 

Taylor Swift's "The Tortured Poets Department" era was one of the best things to come out of the 2020s, but it wasn't exactly born out of sunshine and sweet Valentine's dates. It's the breakup album to end all breakup albums, addressing not one, but two breakups. While Joe Alwyn definitely got a nod, fans surmise that most of the tracks on the album are actually about Swift's short-lived, but intense, tryst with The 1975 frontman, Matty Healy. The duo met in 2014, but didn't become an item until Swift broke up with Alwyn in 2023. It didn't last long and was over in a few short months. Despite the duration, the breakup seemed to have a profound impact on Swift if the lyrics to certain songs are to be believed.

On "The Smallest Man Who Ever Lived", Swift sings, "You tried to buy some pills from a friend of friends of mine. They just ghosted you. Now you know what it feels like," before going in with, "And I don't even want you back, I just want to know, If rusting my sparkling summer was the goal. And I don't miss what we had, but could someone give a message to the smallest man who ever lived?" Healy's mother, British actress Denise Welch, later told Andy Cohen on "Watch What Happens Live" that she was glad the relationship ended. "Obviously, on pain of death, can I talk about that episode? But not being her mother-in-law is a role that I'm glad that I lost," Welch said.

When Taylor Swift announced the Eras Tour, we knew it was going to be big, but did any of us realize it would be as culturally significant as it turned out to be? The marathon schedule saw Swift perform in 21 countries across the globe, belting out her massive catalog of hits in 51 cities. Not only was it the feel-good time the world needed, but it made an incredible amount of money. It was a truly superhuman feat, but let's not forget that Swift is human, just like the rest of us. Her personal life and struggles in the spotlight didn't get put on hold just because she had to perform every night. In April 2023, reports surfaced that Swift had split from her partner of six years, British actor Joe Alwyn.

Never one to shy away from getting back on the horse, Swift was then linked to British rocker Matty Healy, frontman of The 1975. Healy was spotted at one of the "Shake It Off" singer's "Eras" shows, and Swift even returned the favor, so it came as somewhat of a shock when it was over in a hot minute. Our girl doesn't make it a habit of speaking out about her romances, but in the documentary series, "Taylor Swift: The End of an Era," the singer admitted, "I went through two breakups on the first half of this tour, and that's a lot of breakups. There were points in this tour when the tour was the only thing that was really keeping me going in my life. Men will let you down, 'The Eras Tour' never will."