Superstar Taylor Swift is known for her love life almost as much as she’s known for her extensive music catalog. Every song she’s written about the men in her life has become a tapestry of love shared and love lost, dating back to the beginning of her career. Many of these tunes contain myriad emotions, but they also showcase some of the blatant red flags that emerged throughout these relationships.
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For her part, Swift acknowledges that her love life plays a lot into not just her personal life, but her professional one, too. “I am sort of a hopeless romantic,” she admitted to Extra. “The idea of romance is kind of what gets me out of bed in the morning.” Now that she’s in a committed relationship with NFL star Travis Kelce, it’s become more apparent just how challenging some of her past relationships were when it comes to sorting through the negativity.
She and Joe Jonas took out their angst in song
Back in 2008, Taylor Swift and Joe Jonas were a true teenage dream when they coupled up and subsequently covered thousands of tabloids. However, the truth about Swift and Jonas’ relationship was more dramatic and brief than the public initially thought. Fans learned that Jonas wasn’t the princely character he was made out to be after Swift infamously called him out on an episode of “Ellen,” saying that he dumped her in a quick and brutal fashion. “When I find that person that is right for me, he’ll be wonderful and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she told the talk show host.
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Swift went on to allegedly write about their brief romance in her song “Forever and Always,” with the lyrics lamenting the breakdown of their relationship. For his part, Jonas also allegedly fired back on the Jonas Brothers’ track “Much Better,” saying, “I get a rep for breakin’ hearts/Now I’m done with superstars/And all the tears on her guitar/I’m not bitter.”
But a few years and several high-profile relationships later, the two seemingly made up, with Swift publicly acknowledging the drama years later. “Yeah, that was too much,” Swift joked on “Ellen” in 2019. “I was 18. We laugh about it now, but that was mouthy … just teenage stuff there.”
She shared Lucas Till with Miley Cyrus
While it’s unclear whether or not Taylor Swift and Miley Cyrus are still friends, they were definitely known to once share the same taste in men. In 2009, both stars were involved with then-rising actor Lucas Till. Till first caught attention starring as Cyrus’ love interest in “Hannah Montana: The Movie,” which also featured Swift in a cameo role. Around that same time, Till appeared as the object of Swift’s affection in her music video for “You Belong With Me.” Teen magazines plastered pictures of the three all over their covers, and fans speculated about the love triangle, though neither relationship was deeply publicized.
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While both Swift and Cyrus kept relatively mum about their short-lived relationships with the “X-Men: First Class” star, Till himself wasn’t as silent. In a 2009 interview, he was asked the tricky question: which of the two entertainers was the better kisser. Even worse? He actually answered. “I liked kissing Taylor a little more,” he admitted to the now-defunct MTV News (via Digital Spy). “Maybe I do [have a crush on her]. Maybe I have since I was 16!”
Things were brief (but sweet) with Taylor Lautner
Another hunky teen actor that Taylor Swift spent time with was “Twilight” actor Taylor Lautner. From appearing together in the film “Valentine’s Day” to embracing on stage at the 2009 MTV Video Music Awards (yes, that Video Music Awards), the two Taylors were hot and heavy for a brief moment in time. Yet, their whirlwind romance was over as soon as it began, and the bittersweet ending inspired the songstress to pen one of her iconic break-up songs, “Back to December.” Unlike most of her other relationship songs, this one focused more on the mistakes made on Swift’s part, with her crooning, “So this is me swallowin’ my pride/Standin’ in front of you sayin’ I’m sorry for that night.”
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But more than a decade later, Lautner and his wife, also named Taylor, joined Swift on stage during her record-breaking Eras Tour, signaling that all bad feelings were lost with time. Lautner and his wife discussed the special moment on their podcast, “The Squeeze.” “[Swift] is the sweetest human being on Earth, so it kind of was just a perfect situation,” Lautner gushed in the episode.
She hooked up with the much older, known ladies’ man John Mayer
After moving on from her break-up with Taylor Lautner, Taylor Swift broke the norm from the young Hollywood heartthrobs and briefly dated the much-older John Mayer. At the time, Swift was 19 and Mayer was 32, and they began a short but serious affair after collaborating on his single “Half of My Heart.” But by the time Swift released her album “Speak Now” in 2010, the truth about Swift’s relationship with Mayer was revealed to the world through a series of damning songs. This included the now-infamous “Dear John,” which blasted the older singer with lyrics that included “I lived in your chess game/But you changed the rules every day.”
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Mayer reportedly responded with his own break-up song, “Paper Doll,” but not before blasting the “Sparks Fly” singer in the press for using her gifts to embarrass him in song. “I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!'” he admitted to Rolling Stone. Ironically, Mayer went on to famously date (and dump) another pop singer — Katy Perry, who is known for holding her own diss track competition with Swift.
She later alluded to all the signs that led to her split with Jake Gyllenhaal
John Mayer wasn’t the only brooding older man that Taylor Swift dated. Her time spent in the fall of 2010 with actor Jake Gyllenhaal later became the stuff of legend, especially after releasing the “All Too Well (Taylor’s Version)” music video in 2021 as it gave fans alleged clues about how the romance turned heartbreak. In the video, which many Swifties believe is about her fraught relationship with the “Donnie Darko” star, stars Dylan O’Brien and Sadie Sink portray a feuding couple, playing out their angst while Swift sings “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.”
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While Swift hasn’t spoken directly about her former flame, Gyllenhaal eventually spoke out about Swift’s “All Too Well” to deny that it was about him. “It is her expression,” he told Esquire. “Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”
She and Conor Kennedy started dating when he was still school-aged
After her break-up with Jake Gyllenhaal, it was Taylor Swift’s turn to play the older lover. In the summer of 2012, the star entered a relationship with 17-year-old Conor Kennedy, grandson of Robert F. Kennedy. While this wasn’t the first time she dated a younger man (both Taylor Lautner and Harry Styles were also 17 when she dated them), it was the first time that she publicly dated someone still in school and who wasn’t not a performer. Plus, rumors swirled that Swift was “obsessed” with the Kennedy family, especially after she and her beau reportedly crashed a Kennedy wedding and refused to leave.
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The summer love came to an end in October 2012, with sources citing long-distance and Swift’s grueling schedule as the cause. When pressed to talk about their relationship, Swift was mainly coy. “I don’t talk about my personal life in that great detail,” she told ABC News. “I write about it in my songs.” As is her style, she eventually wrote a ballad about her former boyfriend, but this time, not about their breakup. Fans believe that “Begin Again,” off of her “RED” album, describes her optimism about her relationship with Kennedy on the heels of her split from Gyllenhaal.
She and Harry Styles traded lyrical barbs
It was a pop star supercouple for the ages when Taylor Swift and Harry Styles got together in the early 2010s. The then member of One Direction caught Swift’s eye in early 2012, and the two spent a whirlwind year together until reportedly parting ways. The couple, formerly known as “Haylor,” was well-documented by the paparazzi, with photos of the two strolling through Central Park making the rounds on the internet in December 2012. But by the new year, the pair had gone their separate ways.
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In classic Swift style, the Grammy winner took to her songwriting to lament the end of her romance with the fellow entertainer. Along with the aforementioned track, she wrote several songs for her album “1989” that were allegedly about their relationship, including “Out of the Woods” and “Is It Over Now?” The latter of which was released in the “Taylor’s Version” edition of the album in 2023. Styles, in turn, penned One Direction’s hit “Perfect” with some rumored remarks about his ex-girlfriend: “If you’re looking for someone to write your breakup songs about/Then baby I’m perfect.”
The two eventually buried the hatchet, even reuniting at the Grammy Awards in 2021 and 2023 to exchange pleasantries. But fans of both artists still see the remnants of the romance that was in their lyrics years later. “To write a song about somebody else and for somebody else to do that, it’s like flattering, even if the song isn’t that flattering,” Styles shared on “The Howard Stern Show.”
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Calvin Harris was reportedly intimidated by her fame
Though it lasted a brief 15 months, the relationship between Taylor Swift and DJ Calvin Harris was a star-studded spectacle. But what really happened between Swift and Harris ended up making their breakup messier. According to an anonymous source, Harris was reportedly “intimidated” by his girlfriend’s fame, which made him avoid accompanying her to events where she would be accepting awards. He eventually broke up with her, citing their age difference as another factor for their separation. “Taylor somewhat lacks real-life experience,” a source told People.
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Things got testy when Harris responded to a report that Swift was allegedly the person who really wrote Harris’ hit “This Is What You Came For.” He called his famous ex out in a series of since-deleted tweets, saying, “You need someone new to try and bury like Katy ETC, but I’m not that guy, sorry. I won’t allow it” (per People). At the time, Swift was famously feuding with Katy Perry and Kim Kardashian, inspiring her infamous “Reputation” era. He later took ownership of his behavior, telling British GQ, “When it ended, all hell broke loose. Now I see that Twitter thing as a result of me succumbing to pressure. It took me a minute to realise that none of that matters.”
Tom Hiddleston wanted to be more public with their relationship
During the summer of 2016, Taylor Swift moved on from her messy breakup with Calvin Harris by spending some quality (and heavy PDA) time with actor Tom Hiddleston. After meeting at the Met Gala, the pair vacationed together with friends and appeared frequently together in Instagram photos. While Swift never spoke publicly about the “Loki” actor, Hiddleston was keen on praising his lady love to the press. It was this type of behavior that reportedly led to Swift calling things off after a few months. “Taylor knew the backlash that comes with public displays of affection,” a source told US Weekly. “But Tom didn’t listen to her concerns when she brought them up.” Later, Hiddleston acknowledged that what the pair had was “real,” but the relationship taught him to better guard his private life from the public eye. “I’m protective about my internal world now in probably a different way,” he told The New York Times. “That’s because I didn’t realize it needed protecting before.”
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Her and Joe Alwyn’s personalities didn’t mix long-term
Taylor Swift’s longest public relationship to date was with British actor Joe Alwyn. The two were together for six years and even ended up writing songs together for her albums “Folklore” and “Evermore.” “I say it was a surprise that we started writing together, but in a way, it wasn’t because we have always bonded over music and had the same musical tastes,” Swift revealed in an Apple Music interview. But even after making sweet music together, the duo called things off in 2023. Sources claimed that even after such a long time together, the “Folklore” artist didn’t see them meshing well in the future. “The differences in their personalities have also become harder to ignore after years together,” insiders shared with People. “They’ve grown apart.”
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Now, the shady side of Swift’s ex Alwyn is no secret anymore, and Swift used her talents to share supposed secrets about the pain she felt during their relationship. “I sent you signals and bit my nails down to the quick/My face was gray, but you wouldn’t admit that we were sick,” she lamented on “You’re Losing Me.” There were even rumors that Alwyn had cheated on his famous flame with his co-star Emma Laird from “The Brutalist,” but nothing has been publicly confirmed. Alwyn eventually addressed their split after years of staying relatively silent. “I think I’ve done what lots of people who find themselves in the public eye do, which is just try and ignore it,” he told The Guardian.
She was fast (and furious) with Matty Healy
Shortly after her six-year-long relationship with Joe Alwyn, and in the midst of her record-breaking Eras Tour, Taylor Swift embarked on a tumultuous fling with Matty Healy, the rebellious frontman of The 1975. While the true timeline of their relationship confirms what we suspected – they initially met in 2014 and had flitted in and out of each other’s lives since — they put things into high gear when they officially got together in May 2023. Between appearances on stage during the Eras Tour and hitting up fashionable hotspots in NYC, the paparazzi descended upon the pair. But within a few months, their hot summer fling fizzled, and the pair had separated.
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By the time Swift released her album “The Tortured Poets Department,” Swifties pointed to several scathing songs being about the rocker, including “The Smallest Man Who Ever Lived:” “I just want to know/If rusting my sparkling summer was the goal … You deserve prison, but you won’t get time/You’ll slide into inboxes and slip through the bars.” Swift herself never spoke publicly about the fling, and Healy chose to brush it off when asked about it. “I haven’t really listened to that much of [the album], but I’m sure it’s good,” he told TMZ.
