Taylor Swift performing during the Eras tour

All of Taylor Swift’s Boyfriends In Order

Taylor Swift’s romantic life has played out against a brilliant setting of chart-topping hits and memorable anthems. But let’s be clear: Taylor Swift is a genius at orchestrating her own story.

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It’s ever so easy for society, with its magnifying glass perpetually held over women’s personal lives, to fabricate stories about irrational romantic attachments and promiscuity. Yet, Swift deftly flips the script in a display of unrepentant girl power. 

Her romances, with Joe Jonas to Joe Alwyn, aren’t a testament to a woman lost in love but a reflection of a fiercely independent spirit exploring life on her own terms. In every whisper of heartbreak or passionate fling, there’s an undercurrent of her autonomy, an unapologetic embrace of her choices. After all, a woman’s narrative isn’t defined by who she dates but by how she owns her story, and here’s a list of the men who have played a role or two in Taylor Swift’s romantic journey. 

1. Joe Jonas (2008)

Joe Jonas in 'See No More' music video

Taylor Swift and Joe Jonas: a throwback to a time when side bangs were the rage and teen anthems blared from flip phones. Both at the budding brink of their careers, the twosome embarked on a whirlwind romance that was more short-lived than a 2000s ringtone. But while their romantic rendezvous may have faded faster than the Jonas Brothers’ early hair straightener phase, it gifted the world with a few melodic gems. 

Let’s not forget that legendary 27-second breakup call, a moment that—while arguably less than ideal—gave us lyrical treasures worthy of every breakup playlist. Now, isn’t it a tad poetic that a relationship lasting mere months could inspire ballads echoing through the ages? 

2. Lucas Till (2009)

Lucas Till and Taylor Swift 'You Belong with me' video

Lucas Till and Taylor Swift’s relationship is a blink-and-you-might-have-missed-it chapter in the balladry of Swift’s romantic repertoire. The duo crossed paths on the set of “You Belong With Me.” While Till played the quintessential boy-next-door in the music video, off-camera, their sparks seemed more akin to the flicker of a candle than a roaring bonfire. 

But as any Swiftie knows, even ephemeral flings in Taylor’s world can offer moments as iconic as the glasses she donned in that video. Though the pair may not have embarked on a long and winding romance, their brief encounter is a testament to the unpredictability of young love.

3. Taylor Lautner (2009)

Taylor Lautner in 'Twilight'
(Summit Entertainment)

The tale of Taylor and Taylor—now there’s a serendipitous serenade. Two rising stars, one iconic name, navigating the choppy waters of Hollywood, and, for a fleeting moment, finding solace in twinning… names at least. Under the glare of paparazzi flashbulbs, Lautner, fresh from his werewolf escapades, and Swift, with her trusty guitar, gave us a whirlwind romance that felt straight out of a fairy tale. 

While their courtship might have been briefer than a cameo appearance, it birthed the poignantly reflective ballad “Back to December.” Swift’s wintry apologies echoed a maturity and depth, suggesting that perhaps there was more to this Taylor x2 equation than met the eye. 

4. John Mayer (2009-2010)

John Mayer - 'New Light' music video

The charts braced for impact when the country darling with her diary-like lyrics met John Mayer, the bluesy crooner known for his complicated romantic sheet music. While shorter than Mayer’s list of hits, their liaison certainly didn’t shy away from the spotlight. And if there’s anything we’ve learned from Swift’s illustrious career, it’s that heartbreak often breeds hit tracks. 

Enters “Dear John.” The song showcased Swift’s ability to turn tumultuous romances into tuneful treasures. While both artists have strummed to newer rhythms and romances, their brief duet on the love stage is a heartbreaking reminder: In the great concert of relationships, not all duets are destined for encores.

5. Jake Gyllenhaal (2010-2011)

Jake Gyllenhaal in 'Enemy'
(Entertainment One)

When Taylor Swift’s diary collided with Jake Gyllenhaal’s indie charm, it was less a meeting of minds and more a symphony waiting to be penned. Who can forget the infamous scarf at the Gyllenhaal family home, a detail as intriguing as the actor’s filmography and one that, we suspect, will forever be shrouded in mystery. 

Although shorter than a brisk New York autumn, their love story has been immortalized in verses as intricate as the plot of a Gyllenhaal movie. “All Too Well,” arguably Swift’s magnum opus, is to their romance what method acting is to Jake: intense, profound, and unforgettably raw. 

6. Conor Kennedy (2012)

Connor Kennedy and Taylor Swift
(screengrab via YouTube

When Taylor Swift ventured into the Kennedy compound, it wasn’t just a merging of melodies and dynasties but a cute dalliance that seemed straight out of a summer novel. Taylor Swift and Connor Kennedy’s romance, as fleeting as summer in New England, was nonetheless poignant. 

Between yacht getaways and antique-filled mansions, one could almost hear the distant echoes of “Begin Again” wafting through the Hyannis Port breeze. Swift, ever the lyrical laureate, didn’t shy away from sprinkling hints of this sun-kissed romance in her tracks. 

7. Harry Styles (2012-2013)

Harry Styles looking upset in Don't Worry Darling.
(Warner Bros. Pictures)

The Styles-Swift saga: a union so stylish it almost demanded its own fashion line. With Central Park strolls and snowmobile rides, their courtship felt like a pop culture crossover episode we didn’t know we needed. 

Although their duet in the game of love lasted shorter than a British summer, it was rife with moments as iconic as Styles’ patterned suits. “Out of the Woods,” with its haunting refrain, could well be the soundtrack to their winter wonderland romance.

8. Calvin Harris (2015-2016)

Calvin Harris 'Summer' music video

When the Nashville songbird met Scotland’s beatmaster, it was less a mashup and more a harmonious blend—think whisky meets sweet tea. For a while, these two lit up the charts, and Instagram feeds alike, with swan floats and beachside escapades that made mere mortals reconsider their vacation goals. 

Their alliance, brighter than Harris’s neon DJ booth, seemed destined to set the soundtrack of summer. But, as with many a chart-topping banger, the crescendo eventually gave way to a quieter coda. Their romance still birthed anthems (and perhaps a few DJ mixes) that had us all dancing in joy and reflection. Swift’s “Getaway Car” was just the lyrical escape we were looking for.

9. Tom Hiddleston (2016)

Tom Hiddleston as Loki in Marvel Studios' LOKI, Season 2, exclusively on Disney+. Photo courtesy of Marvel Studios. © 2023 MARVEL.
(Marvel Studios)

‘Hiddleswift’ surprised everyone and the brief but engaging chapter in which Loki encountered love songs simply couldn’t be ignored. From Rhode Island rendezvous to Roman ruins, their short love story was punctuated by that now-infamous “I ❤️ TS” tank top—a sartorial choice as audacious as Hiddleston’s Loki himself.

For a brief but unforgettable period, “Hiddleswift” provided a fascinating insight into a union where two seemingly divergent universes merged. Their story was as engaging as Swift’s songs or Hiddleston’s on-screen performances.

10. Joe Alwyn (2017-2023)

Joe Alwyn in Conversations with Friends

Taylor Swift and Joe Alwyn’s love story began with subtlety, sidestepping the usual paparazzi fanfare. Perhaps it was the allure of Alwyn’s British reserve or the serenity of Swift’s post-‘Reputation’ era, but their union was refreshingly devoid of dramatic headlines. Instead, clandestine London rendezvous and lyrically encrypted love notes became their M.O. 

So fans were shocked when Swift and Alwyn called it quits in 2023 after a solid six-year run. Despite the inevitable heartbreak, Swift and Alwyn have kept their friendship. They both expressed gratitude for their time together and wished each other well in the future.

11. Matty Healy (2023)

Matty Healy of The 1975 performs onstage
(Kristy Sparow/Getty Images)

Taylor Swift and Matty Healy were first spotted together in May 2023 and were quickly inseparable. They were seen holding hands, kissing, and even attending each other’s concerts. However, by June, it was reported that the pair had split up. 

According to sources, the relationship was “just a fling,” and they were both too busy to commit to a serious commitment. Thanks to Healy’s less-than-stellar reputation, only a few swifties were thrilled about this duo, so when their short-lived love affair went from a fiery blaze to a rather lackluster fizzle, not many tears were shed.

12. Travis Kelce (2023-present)

Taylor Swift and Travis Kelce at Waverly Inn

Whether we like it or not, we are in the midst of a relationship storm between Taylor Swift and Travis Kelce, the most unlikely couple of the year. 

Since September 2023, the rumors of a romance between the two have persisted. These two have been seen together multiple times after their initial sighting at a Kansas City Chiefs game. However, neither Swift nor Kelce have confirmed or denied the rumors.

(featured image: Variant Films)

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Image of Faith Katunga
Faith Katunga
Faith is a freelance journalist with an insatiable curiosity for all aspects of current events, from the global economy and fashion to pop culture and travel. She watches an absurd number of cat videos on Instagram when not reading or writing about what is going on in the world. Faith has written for several publications, including We Got This Covered, Italy Magazine, TheTravel, etc., and holds a master's degree in Fashion Culture and Management.