Taylor Swift is no stranger to the spotlight – both for her chart-topping hits and her high-profile romances. The pop sensation, known for her string of famous exes, has a knack for turning her relationships into lyrical masterpieces that leave us all wondering, “Who’s next?” She’s currently rumoured to be dating Kansas City Chiefs footballer Travis Kelce, and we can’t wait to see how this unfolds and if she’s finally going to get her happy ending. In the meantime, grab your popcorn, folks, because today, we’re about to take a thrilling ride through Taylor Swift’s boyfriend list.
Are you ready for it? Let’s dive into her long list of ex lovers.
Taylor Swift’s exes: A list of all her famous boyfriends
2008: Joe Jonas
Let’s start with a bang, shall we? The singer’s dating escapades kicked off with none other than Joe Jonas in 2008. But hold onto your hats, because this one was a rollercoaster. The former Jonas Brother turned DNCE front man delivered the infamous breakup news via a 27-second phone call. Ouch! Taylor’s response? She channelled her heartbreak into songs like “Last Kiss” and “Forever and Always.” Talk about swift (no pun intended) revenge!
Jonas eventually went on to wed Game of Thrones actress Sophie Turner, only for their four-year marriage to end in an acrimonious divorce that has been tabloid fodder since September 2023. Both parties are currently in a custody battle over where their two daughters will live — in the US with Jonas, or England with Turner.
Interestingly, Swift, who has been longtime friends with Turner for years, has taken her pal’s side and is even temporarily housing Turner in her New York City apartment. The two have been spotted on multiple outings together, including supporting Swift’s new beau Travis Kelce at a recent NFL game against the Jets.
Hilariously enough, Swift has a song titled “Vigilante Sh-t“, which so aptly contains the line “picture me thick as thieves with your ex-wife”.
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2009: Taylor Lautner
Ah, the age of Taylor Squared. Swift and Taylor Lautner fell for each other on the set of Valentine’s Day, but their romance was short-lived. Rumour has it that Lautner was more smitten than Swift, leading to their breakup. The apology song, “Back to December,” speaks volumes about their relationship. Swift also made it clear she was contrite at her 2010 American Music Awards performance, where she did a mashup of the song with One Republic’s “Apologize”.
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2009-2010: John Mayer
When age gaps and love collide, you get Swift’s tryst with John Mayer. It was a time when the world was buzzing about their union, mainly because of their significant age gap – she was 19, and he was 32. This age disparity became a sore point that scored its own famously heart-wrenching lyric in Swift’s song “Dear John”, which she penned after their breakup — “Don’t you think nineteen’s too young/ To be played by your dark, twisted games when I loved you so?”
Their story didn’t end there; they collaborated on music during their brief romance. In the years to come, they would take jabs at each other through their songs. However, it’s fair to say that many people found themselves on Team Swift in this lyrical debate. Now, it’s no secret that some of Taylor Swift’s exes seem to have bad blood with the singer, and it’s safe to say that John Mayer isn’t exactly her favourite mistake on her boyfriend list.
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2010: Jake Gyllenhaal
Cue the heartstrings and memories of autumn leaves, because next up is Jake Gyllenhaal. Their brief romance back in 2010 is something that fans know “All Too Well.” The two lovebirds strolled arm-in-arm on Thanksgiving and spent their December birthdays apart. While they’ve remained tight-lipped about their relationship, fans are convinced that several tracks on Taylor Swift’s “Red” album were inspired by Jake.
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2011: Zac Efron
High School Musical star Zac Efron and Swift reportedly had a “thing”. Rumour has it that their love story was short-lived but sweet, and they even spontaneously sang a super fun parody version of “Pumped Up Kicks” by Foster The People together to debunk the dating rumours.
Both Swift and Efron have consistently denied any romantic involvement. They both appeared on Ellen DeGeneres’ talk show in February 2012, where the host playfully teased them about being a couple. This banter continued when Swift returned to Ellen’s show in 2013, with the host inquiring about Zac Efron. Swift promptly clarified, “We actually never dated. I don’t know, I haven’t talked to him in a while because we didn’t date.”
Some mysteries may remain unresolved for Swifties, but that’s perfectly alright. We still have the right to think about what could have been though… right?
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2012: Conor Kennedy
Swift and Conor Kennedy shared a whirlwind romance, believed to be the inspiration for her song “Begin Again.” Their relationship began when Swift was spotted with the Kennedy political family during a 4th of July gathering in Hyannis Port, Massachusetts. Interestingly, Swift’s connection with the Kennedys started a year earlier when she befriended Conor’s aunt, Rory Kennedy, after Rory reached out to Swift for concert tickets in 2011. This connection deepened when Swift attended the Sundance Film Festival’s screening of Rory’s HBO documentary, Ethel, in January 2012, further solidifying her bond with the Kennedy family.
Critics raised concerns about the significant age gap between Swift and Kennedy during their relationship in 2012. At the time, Swift was 23 years old, while Kennedy was only 18 and still in high school.
According to Radar Online, Conor Kennedy and Swift parted ways because she allegedly approached the relationship with excessive seriousness and intensity. An insider close to Kennedy explained that Conor, being an 18-year-old, wasn’t prepared for such a serious commitment, while Swift was apparently searching for a soulmate, which made him uncomfortable due to the intensity of her feelings. The source further suggested that Swift’s interest seemed more focused on the idea of dating a Kennedy rather than Conor himself.
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2012-2013: Harry Styles
Taylor Swift and Harry Styles, two music industry heavyweights, embarked on a high-profile romance that captured the attention of fans and the media alike. Their relationship timeline was a rollercoaster of highs and lows. It all began in late 2012 when they were spotted on a romantic stroll through Central Park in New York City. The budding romance made headlines, and the couple’s public outings and affectionate displays fuelled the frenzy. Swift and Styles seemed to hit it off, and their mutual interest in songwriting and performing brought them even closer.
The high points of their relationship included their trips around the world together, romantic getaways, and even a skiing adventure in Utah. Both being artists, they shared a deep connection over music, and it was rumoured that they collaborated on a few songs during their relationship. However, the high-profile nature of their romance also brought intense media scrutiny and fan attention, which eventually took a toll.
The low points began when they reportedly had a heated argument during a vacation in the British Virgin Islands, leading to their highly publicised breakup in early 2013. Their split resulted in a flurry of songwriting from both sides, with Swift penning songs like “I Knew You Were Trouble” and “Out of the Woods,” while Styles contributed to One Direction’s track “Perfect.” Their relationship timeline was a whirlwind, leaving an indelible mark on both their personal lives and their music careers.
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2015-2016: Calvin Harris
Swift and Calvin Harris had a long and well-documented romance, complete with red carpet appearances and social media posts. But it was Harris who reportedly wanted to end things. While neither of them publicly confirmed it, Taylor’s hit “We Are Never Ever Getting Back Together” was widely believed to be about Harris. However, some die-hard Swifties remain convinced that this song is about a different ex-lover, adding a layer of mystery to her lyrical narratives.
Their relationship, which lasted 15 months, left its mark on several of Swift’s songs, including “I Did Something Bad,” “Getaway Car,” “I Forgot That You Existed,” “Bejeweled,” and “High Infidelity.” The drama even spilled into her music, as evidenced by the song “Coney Island” from her album ‘Evermore,’ where she sings about the moment Harris failed to mention her name during a speech at the 2016 GQ-Men of The Year Awards.
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2016: Tom Hiddleston
Remember Hiddleswift? Taylor Swift and Tom Hiddleston’s whirlwind romance took the world by storm in 2016. Their high-profile relationship began shortly after Swift’s breakup with Calvin Harris, and it was marked by a series of headline-making moments. The couple was first photographed dancing together at the Met Gala in May, and the images of them twirling around the dance floor went viral. Their chemistry was palpable, and it didn’t take long for the media to dub them “Hiddleswift.” They were soon spotted travelling together, from Rhode Island to Rome, and their public displays of affection were hard to miss. Hiddleston even wore a tank top with “I Heart T.S.” emblazoned on it during a beach outing, sparking further media frenzy.
Despite the initial excitement, their relationship faced some low points. The constant media attention and speculation took a toll on their privacy, and sceptics began questioning the authenticity of their romance, suggesting it might be a publicity stunt. Additionally, Swift had recently come out of a high-profile breakup, which raised eyebrows about the speed at which she and Hiddleston became a couple. The strain of the spotlight and the pressures of a highly scrutinised celebrity relationship ultimately led to their breakup in September 2016, less than three months after they were first spotted together. While their romance was short-lived, it remains a notable chapter in Swift’s dating history.
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2017-2023: Joe Alwyn
Taylor Swift’s boyfriend list may be a long one, but the singer has surely shared some genuine and passionate connections with some of her exes. Now, let’s take a closer look at the star’s most enduring relationship to date – her love story with Joe Alwyn. This union was unlike any other in Swift’s dating history, as the couple kept their romance meticulously private, away from the prying eyes of the media. Their journey began in 2017 when they were first photographed together in Nashville, sipping coffee on a balcony. What followed was a relationship that spanned a remarkable six years, ending in April 2023, leaving fans both surprised and saddened.
Their amicable breakup in April 2023 marked the end of an era, as Taylor herself would say. She even released the breakup song ‘You’re Losing Me,’ offering her perspective on the relationship’s conclusion. The lyrics suggest that their paths had simply diverged, with the man in the song, presumably Alwyn, not wanting to marry her. The intricacies of their relationship continue to be a subject of fascination among fans, with many still cherishing the memories of their years together. Well, all we can say is another one bites the dust on Taylor Swift’s boyfriend list.
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2023: Matt Healy
The 12-time Grammy-winning superstar, Taylor Swift, aged 33, and Matty Healy, the 34-year-old frontman of The 1975, had been friends since 2014, and were linked romantically since 2014 up until 2023. The encounter between Healy and Swift took place backstage in Los Angeles during one of Healy’s concerts. Swift was in attendance at the show alongside Ellie Goulding and Selena Gomez. Healy later revealed on the Australian radio program Shazam Top 20 how they exchanged contact information.
During the program, the host playfully suggested that he and Swift might become the next major celebrity couple. Healy responded with a sense of awe, saying, “I mean, goodness gracious, what am I supposed to do, date Taylor Swift? She’s an absolute sensation. I wouldn’t turn down that opportunity.”
After years of evading questions and denying rumours about them actually finding love in each other, Healy and Swift emerged as a couple in 2023, leaving fans surprised.
Up until recently, the two seemed to be a number, and finally didn’t try too hard to conceal it. During Swift’s on-going record-breaking Eras Tour that began in April, Healy was seen at all six of her concerts in Nashville and Philadelphia. The pair was also spotted spending quality time together in New York City, from socialising with friends at the Electric Lady recording studio to sharing a kiss at the exclusive members-only club, Zero Bond.
Earlier in June, the news of Taylor and Matt’s split took over the internet and once again, fans were left in dismay. “They are no longer romantically involved,” a source later told Entertainment Tonight . The source further added that owing to conflicting schedules and incompatibility, the two had decided to part ways.
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2023: Travis Kelce (Rumoured)
And last but not least, we have the latest entry in Taylor’s dating history – Travis Kelce. This unexpected entry into Taylor’s love life has raised eyebrows and piqued curiosity among her fans. Kelce, a 33-year-old NFL player for the Kansas City Chiefs, first expressed his interest in Swift on his podcast, ‘New Heights.’ He shared an endearing anecdote about crafting friendship bracelets for her with his phone number, only to be disappointed when she didn’t meet with him.
However, the plot thickened when gossip site DeuxMoi, known for sharing anonymous submissions from the public, reported sightings of the two having dinner together in September. While the rumours swirled, some sources suggested they were “quietly hanging out,” yet others clarified that they were “not officially dating.” Despite the ambiguity, Swift’s appearance at a Kansas City Chiefs game, donning the team’s red and white colours in a private box, fueled further speculation.
It’s safe to say that Travis Kelce’s dream of meeting Taylor Swift and giving her his number has sparked a bit of a pipe dream in the world of celebrity romances. Will this be the beginning of a new chapter in Swift’s love life? Only time will tell, and Swifties around the world will be keeping a close eye on this intriguing development in Taylor Swift’s boyfriend list.
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As we come to the end of Taylor Swift’s boyfriends list, we’d love to know which of these famous men did you find the most compatible with the singer?
Frequently Asked Questions (FAQs)
Who is everyone Taylor Swift dated?
John Mayer, Harry Styles, Joe Alwyn, Joe Jonas, Tom Hiddleston, Matt Healy and others.
Who is the longest bf of Taylor Swift?
Out of Taylor Swift’s exes, her relationship with Joe Alwyn was the longest (7 years).
How many boyfriends has Taylor Swift had?
Taylor Swift has 12 publicly known exes.
Who was the first famous person Taylor Swift dated?
Reportedly, Joe Jonas.
Did Ed Sheeran and Taylor Swift date?
While they’ve been good friends for years, Sheeran has previously slammed speculation that he was dating Swift. During an interview with Rolling Stone in 2017, he criticised an article that claimed he dated the singer while on tour together in 2013.
This story first appeared on Prestige Online Singapore
