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It’s a rite of passage to listen to Taylor Swift after experiencing terrible heartbreak. The country-pop singer is the queen of crafting the most relatable hits that can get us through the most horrific breakups imaginable. But while her breakup songs are incredibly healing for the general public, they can occasionally be to the detriment of some of her past romantic partners. Some of Swift’s most popular songs are about her ex-boyfriends. And although Swifties love to speculate over who the pop star is crooning about in any given track, Swift is adamant about not giving this information away. “I never disclose who my songs are about,” she told Glamour back in 2012.
Still, fans are quick to speculate. It sometimes changes the way Swifties perceive her former partners, whether that’s for better or (more often than not) for worse. Some of her ex-boyfriends have even received a swarm of hate from her fans based purely on the assumption that certain unflattering song lyrics are written about them. But from Swift’s point of view, her exes sort of have it coming to them for dating a songwriter in the first place. As she told New York Magazine (via Vulture), “I heard from the guy that most of ‘Red’ is about. He was like, ‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’”
With that being said, what exactly have all of the Grammy winner’s exes said about the songstress following their breakups?
Joe Jonas
Back in 2008, you couldn’t stumble upon a single teeny-bopper magazine without seeing either Joe Jonas or Taylor Swift plastered to the cover. So when word spread that the country-pop star and the member of the Jonas Brothers were in a romantic relationship, it felt as though two worlds were colliding. The high-profile duo only dated for a handful of months back in 2008. But despite the short-lived nature of the romance, their breakup ended up becoming headline-worthy news. Shortly after their split, Swift famously admitted on “The Ellen DeGeneres Show” that Jonas dumped her over the phone. If it wasn’t already bad enough that the “Sucker” singer couldn’t even end the relationship in person, according to Swift, the phone call lasted less than 30 seconds.
Although it wasn’t the kindest way to end things, Swift admits that her ex-beau didn’t deserve the public shame that she thrust upon him following the split. Not only did she call him out on “Ellen,” but she also wrote an entire song about the breakup, called “Forever & Always,” that paints Jonas in a bad light. Now, Swift regrets how she reacted to the situation. “That was too much,” she reflected when she returned to “The Ellen DeGeneres Show” a full decade later. To further prove they are on good terms, Jonas sat down with Entertainment Tonight in 2019 to emphasize that it’s all water under the bridge. He said, “I’ve moved on. I’m sure Taylor’s moved on. … We’re all friends. It’s all good.”
Lucas Till
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Remember Lucas Till? He was the country heartthrob of 2009, best known for his role in “The Hannah Montana Movie” and Taylor Swift’s award-winning “You Belong With Me” music video. In the iconic video, Till and Swift star as best friends who are secretly in love. But as is the case for any good romance story, a central conflict is keeping them from being together — that conflict being that Till is already in a relationship with someone else. But in real life, Till and Swift’s lack of conflict with one another seems to be what drew them apart. From Till’s perspective, their relationship was simply too, well, friendly. And often times when you’re a teenager, that “Romeo & Juliet” passion is more valuable than a stable, healthy dynamic.
He explained his reasoning for cutting ties with the pop star in 2009. “We dated for a little bit,” Till spilled to MTV News. “But there was no friction because we were too nice. We just really both liked each other, [but] most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that [it] didn’t work out.”
Taylor Lautner
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Middle schoolers across the nation lost their minds in 2009 when Taylor Lautner and Taylor Swift began dating after meeting on the set of “Valentine’s Day.” However, they were only together a few months, and soon enough, the actor became the subject of his own song: “Back to December.” The lyrics, which read like an apology, appear to imply that they simply weren’t on the same page. “You gave me roses and I left them there to die,” Swift sings. “So this is me swallowing my pride standing in front of you saying I’m sorry for that night.”
As Lautner later confirmed on a December 2023 episode of the “Call Her Daddy” podcast, Swift was in fact the one who called things off, but there were no hard feelings. The pair remained friendly but eventually lost touch before turning things around in 2023. “I think when you respect somebody for who they are, like, in their soul, it allows you to move on, forgive, and continue that, you know, love in a different way,” he mused, gushing, “Honestly, I would say one of the greater things to happen in my life over the last year is the rekindling of our friendship.” Indeed, Lautner was cast in Swift’s 2023 music video for “I Can See You” and even joined his ex on-stage during her Eras tour stop in Kansas City, Missouri. What’s more, he was caught backflipping at a private screening of the “Eras Tour” film — a clear sign of approval.
Cory Monteith
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Shortly after she called it quits with Taylor Lautner, Taylor Swift reportedly dated Cory Monteith for about a month. While the singer never addressed the rumors, Daily Mail spotted the pair hugging at a bowling alley in Los Angeles in 2010. The purported date came just two months after they were photographed together at the Grammys. However, despite all of the speculation, Monteith denied any romantic connection, telling The Ellen DeGeneres Show, “We’re just friends.” And while he praised Swift, noting “she’s lovely,” he was adamant they were not an item. This didn’t stop fans from speculating that Swift’s 2010 song called “Mine” was written about the “Glee” star.
Indeed, the singer confirmed to Yahoo! (via MTV) that the track was about a failed love connection, and the timing would surely match up. “This is a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes,” she shared. Explaining that the relationship ended shortly after she wrote the track, she said they lost touch, but he reached out to her after the song’s release to ask if it was about him. “I was like, ‘Yes!’ because that one was sort of half-confession and half-prediction or projection of what I saw,” she told the outlet.
John Mayer
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John Mayer and Taylor Swift were romantically linked when the “Lover” singer was only 19 years old. In Swift’s song “Dear John,” which is allegedly written about Mayer, she doesn’t paint him in the best light. In fact, she depicts the musician as a tumultuous boyfriend who took advantage of the fact that she was significantly younger than him. (Mayer was 32 at the time, making him 13 years her senior.) While most of Swift’s songs are a lot more ambiguous regarding who she’s singing about, “Dear John” literally uses her ex’s name in the title. With lyrics like, “Dear John, I see it all now that you’re gone / Don’t you think I was too young to be messed with?” fans were quick to assume it was about Mayer.
But unlike Taylor Lautner, who found Swift’s breakup song about him to be beautiful, Mayer had a completely different reaction to his ex writing lyrics about him. “It made me feel terrible, because I didn’t deserve it … and I never did anything to deserve that,” the “Neon” singer told Rolling Stone back in 2012. “It was a really lousy thing for her to do.” He added, “I was really caught off-guard, and it really humiliated me.”
But apparently, the drama between the ex-lovers refuses to die down. According to a 2021 Paper magazine article, Mayer has allegedly received constant death threats from Swift’s diehard fans, to which Mayer has responded. He reportedly asked one Swiftie, “Do you really hope that I die?”
Jake Gyllenhaal
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Taylor Swift has built a name for herself in part by writing emotional tracks about her ex-partners. Yet it’s arguable that her most passionate and heartfelt songs are dedicated to Jake Gyllenhaal, whom she dated in the fall of 2010. Her songs “All Too Well” and “We Are Never Getting Back Together” from her “Red” album are allegedly written about Gyllenhaal, and they don’t exactly paint him in the best light, either. But despite everything, Gyllenhaal still spoke highly of Swift long after their breakup, saying on “The Howard Stern Show” back in 2015, “She is a beautiful girl.”
But things didn’t end there. In 2022, when Swift released “Taylor’s Version” of the “Red” album, a lot of the artist’s fans were quick to attack Gyllenhaal for breaking Swift’s heart all those years ago. In an interview with Esquire, Gyllenhaal commented on the whole situation. He said that although Swift has the right to artistic expression and that she can sing about whatever she wants, he also believes she has a responsibility to ensure her fans do not attack him online (which they allegedly have in swarms). As he told the magazine in 2022, “There’s anger and divisiveness, and it’s literally life-threatening in the extreme.”
Harry Styles
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Taylor Swift and Harry Styles only dated for about three months back in 2012, but the relationship gave Swift plenty of inspiration. It’s believed that a number of tracks on her 2014 album, “1989,” are about Styles, including “Out of the Woods” and, unsurprisingly, “Style.” And while some folks may have been bothered by that, it seems Styles wasn’t. Although he coyly told Rolling Stone in 2017, “I don’t know if they’re about me or not,” he later admitted on “The Howard Stern Show” in 2020 that he took the tracks to be a compliment. “I think about what it means to me to write a song about somebody else, and for someone else to do that, I think it’s flattering,” he said. “Even if the song isn’t that flattering, you still spent time on it, and ultimately, using Taylor as an example, she’s a great songwriter.” That sure helps explain how the exes are on such good terms now (they were spotted happily chatting at the 2021 Grammys).
As for what went wrong, Styles told Rolling Stone that their young age and the constant media attention played a big part. At the end of the day, though, Styles said it simply wasn’t meant to be. “Certain things don’t work out,” he mused. “There’s a lot of things that can be right, and it’s still wrong.” And yet, he wouldn’t change a thing. “Meeting someone new, sharing those experiences, it’s the best s*** ever. So thank you,” he enthused.
Calvin Harris
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Fans seemed a bit shocked when Taylor Swift and Calvin Harris began dating, as their respective music genres are so different. Harris is an EDM DJ, while Swift is a pop icon. But apparently, opposites attract because Harris and Swift made it work for over a year together. The couple lasted for a total of 15 months. But as sources report, Harris was the one to call it off with Swift due to one allegedly shocking reason. “[Harris] said on multiple occasions that he was intimidated by Taylor,” an insider close to the “Wildest Dreams” singer revealed to People.
Despite the fact that Harris and Swift’s relationship lasted for over a year, it was their breakup that ended up making more headlines than their actual time spent together as a couple. At first, the ex-partners seemed supportive of each other following their split. But when Swift got credit for Harris’ song, “This is What You Came For,” things began to get ugly. In 2016, Harris blasted Swift and her team for allegedly lying about the fact that she wrote and produced the song rather than him. He said in a now-deleted tweet that it was “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.” Meanwhile, TMZ reported that Swift had, in fact, co-written the song with her former beau.
Tom Hiddleston
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Tom Hiddleston and Taylor Swift had a brief romance in 2015. Although they only dated for approximately three months, Hiddleston, who appeared in “The Avengers,” seemed entirely smitten with Swift. He was even caught wearing a bejeweled “I Heart T.S” shirt while with his former partner, proclaiming his love for the whole world to see.
And despite Swift being the one to break Hiddleston’s heart by calling it quits, the “Loki” actor has nothing but kind things to say about his ex. When he was interviewed by GQ in 2017, he gushed about Swift, saying, “Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time.” Yet not everyone was 100% convinced that the couple was authentic, with some assuming their entire relationship was a publicity stunt, per the Los Angeles Times. Hiddleston was quick to deny this conspiracy, telling GQ, “Of course, it was real.” The song that Swift had allegedly written about the Marvel actor is her hit, “Getaway Car,” from the album “Reputation.”
Joe Alwyn
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Taylor Swift met her longtime romantic partner, Joe Alwyn, at the 2016 Met Gala. But Swift and Calvin Harris had not yet announced her breakup, and she had a whirlwind romance with Tom Hiddleston before dating Alwyn. In 2017, rumors of Swift and Alwyn’s relationship started circulating, and sources said they’d been dating for a while.
Swift made a point of keeping her relationship with “The Favourite” actor out of the public eye. During an interview with British Vogue, Alwyn explained, “I’m aware people want to know about that side of things. I think we have been successfully very private, and that has now sunk in for people. But I really prefer to talk about work.” However, fans got a glimpse of their love story based on some of Swift’s songs that are believed to be written about him. Toward the beginning of their relationship, her album “Reputation” was released with songs like “Gorgeous,” “Delicate,” and “King of My Heart,” presumably about the Hollywood newcomer. She’d later put out songs such as “Lover” and “Invisible String.” Alwyn even tested out his own songwriting skills, collaborating with Swift on tunes like “Exile,” “Betty,” “Champagne Problems,” and “Sweet Nothing” under the pen name William Bowery.
Despite keeping to themselves, these two seemed to enjoy a happy relationship. So, fans were shocked when ET shared the news of Swift and Alwyn splitting in 2023. Just as in their time together, the stars have kept quiet about their breakup as of this writing. However, a source told CNN, “They simply grew apart and plan to remain friends.”
Matty Healy
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Just weeks after her breakup from Joe Alwyn made headlines, Taylor Swift was linked to another Brit: The 1975 frontman Matty Healy. It was May 2023, and a source told The Sun that Swift and Healy were a great match because they understood one another’s careers and supported each other. “She and Matty are madly in love,” the insider said, adding they were constantly texting and video chatting. “It’s super-early days, but it feels right.” Despite those claims of a perfect connection, though, ET confirmed that June that they had already broken up. “They are both extremely busy and realized they’re not really compatible with each other,” a source explained.
Interestingly, Swift and Healy were first said to be dating back in 2014 after Swift attended a couple of The 1975’s concerts and both she and Healy were seen rocking each other’s tour merch. Healy also added fuel to the fire when he called into Australian radio show Shazam Top 20 that November and teased, “We exchanged numbers — let’s see what happens.” He quipped, “She’s a sensation — I wouldn’t say no.” Soon enough, they were romantically linked in the press, but Healy quickly denied those rumors in January 2015. “We exchanged numbers in the same way that a lot of people in this kind of world do, and we spoke occasionally,” he clarified on Shazam Top 20. “There’s no, like, relationship or anything happening.”