A Complete Guide to Taylor Swift’s Dating History | lblthg.com

A Complete Guide to Taylor Swift’s Dating History

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Taylor Swift’s love life has been the subject of the public’s wonders ever since she stepped on the scene in 2006 with her self-titled debut album. Over the years, having released 11 top-charting albums, amassing 14 Grammy awards, and taking the world by storm with her record-breaking Eras Tour, she has only become ubiquitous. As a result, her romances have been placed under bigger and bigger magnifying glasses, especially as she has revealed many of her old flames became writing material for her catchy songs.

From her sweet, teenage puppy love with Taylor Lautner and her exciting summer fling with Tom Hiddleston to her serious, long-term coupling with Joe Alwyn and her “So High School” romance with Travis Kelce, Swift’s dating history has been full of some of Hollywood’s biggest A-listers. Read ahead for all the muses that inspired her top tracks.

Joe Jonas (July-October 2008)

Taylor Swift and Joe Jonas sitting together
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Swift’s first major public relationship was with then-Disney Channel heartthrob Joe Jonas, whom she dated for four months between July and October 2008. The details of their relationship are minimal, barred to some cute photos of them at the 2008 MTV Video Music Awards and a couple of tracks, namely “Forever & Always” and “Mr. Perfectly Fine.” Both songs appear on Swift’s second studio album Fearless, which she released a month after they split.

The record-breaking songstress more or less confirmed she did indeed write “Forever & Always” about the “Burnin’ Up” singer during an appearance on The Ellen Degeneres Show. “Someday, I’m gonna find somebody really, really, really great, who’s right for me,” she shared. “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.”

Over the years, Swift developed a friendship with Jonas’s now-ex-wife Sophie Turner. The actress told British Vogue, “Taylor was an absolute hero to me this year,” amid their divorce, as the “Cruel Summer” singer opened up her New York City apartment to her and her children.

Lucas Till (March-April 2009)

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Swift’s short-lived romance with Lucas Till was a classic case of when life imitates art. The MacGyver actor played the singer’s love interest in the music video for “You Belong With Me,” following their collaboration on Hannah Montana: The Movie the year prior. They were smitten for about a month before calling it quits.

Till confirmed they were an item to MTV, “We dated for a little bit. But, there was no friction because we were too nice,” he said “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 its passionate, and with us I really just liked her as a friend. That’s the only reason that didn’t work out.”

Taylor Lautner (October-December 2009)

Taylor Swift and Taylor Lautner sitting in a car
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It appears Taylor Lautner has a thing for Taylors. Before there was Taylor Lautner and Taylor Dome, there was Taylor Lautner and Taylor Swift. The singer once again fell for her on-screen love interest in real life; the two starred in the rom-com Valentine’s Day.

During their three-month fling in 2009, the pair was captured getting cozy on several dates, including a rink-side outing at a hockey game. In November of that year, Swift gave Lautner a cheeky little shoutout during her Saturday Night Live monologue, in which she sang, “If you’re wondering if I might be dating the werewolf from Twilight…I’m not going to comment on that in my monologue,” before mouthing “Hi, Taylor,” and blowing the camera a kiss.

The same month, she told InStyle, they have “gotten really close.” Lautner also commented, saying, “Taylor is hilarious. It was definitely not hard to play her love interest.”

That might be true, but even still, their romance fizzled out. People confirmed they broke up in December 2009. “It was never a big deal to begin with. The media made way more out of it than it is,” a source close to Swift told the publication. “They went out on a few dates and realized this was just not going anywhere.” They also cited distance, with Swift being in Nashville and Lautner being in Los Angeles, and their busy schedules as contributing factors to their split.

Taylor Swift and Taylor Lautner hugging
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However, Lautner and Swift have remained friends over the years. Swift brought the actor out during her Eras Tour show at Arrowhead, Stadium, in Kansas City on July 7, 2023. Lautner posted a photo to Instagram of himself, Swift, and Dome recreating a Spider Man meme the next day—the same day Swift released her music video for “I Can See You (Taylor’s Version),” in which Lautner stars.

John Mayer (December 2009-February 2010)

John Mayer and Taylor Swift performing on stage together
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Swift first crossed paths with John Mayer after he tweeted about wanting to collaborate with her in March 2009; his wishes came true with “Half of My Heart,” released in November of that year. Swift, then 19 years old, brought the “Gravity” singer , then 32 years old, out during a stop in Los Angeles on her Fearless tour, and they performed together once again at Z100 Jingle Ball in December. The same month, Mayer praised Swift on The Ellen DeGeneres Showsaying, “She’s one of the smartest, most talented people around right now…I think she’s that genuine.”

John Mayer and Taylor Swift hugging
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In January 2010, things seemed to heat up when they were spotted out to dinner in Nashville, but quickly fizzled out as rumors swirled that they split the next month. Mayer did, however, honor Swift at the Songwriters Hall of Fame Ceremony in June 2010; Swift thanked him with a kiss on the cheek and a warm embrace.

In October of that year, Swift released her third album Speak Now, featuring “Dear John,” which is believed to be about Mayer; fans also believe “The Manuscript” off of her eleventh studio album The Tortured Poets Department is also about the singer-songwriter. Meanwhile, in June 2013, Mayer released “Paper Doll,” which many have speculated is about Swift.

Jake Gyllenhaal (October-December 2010)

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Swift and Jake Gyllenhaal’s romance was truly cinematic—which only makes sense that the singer adapted her memories for the big screen with All Too Well: The Short Film, a nearly 15-minute video, released November 2021, that recounts their relationship from their sweet beginnings to their bitter, heart-aching end.

Swift, who was 20 at the time, and Gyllenhaal, who was 29 at the time, were first set up by their mutual friend, Goop founder Gwyneth Paltrow, at a dinner party at the London home Paltrow shared with then-husband Chris Martin. The Iron Man actress admitted to playing cupid to USA Today years later, although she never revealed the date.

The pair was first spotted together backstage at an SNL taping in October 2010. The same weekend, they enjoyed brunch together in Brooklyn. In December, they were photographed on a snuggly winter walk; however, that same month it was confirmed they split. A source told People in January 2011, “They’re over. It ended last month.”

Conor Kennedy (July-September 2012)

Who could forget the chaotic relationship that was Swift and Conor Kennedy (a.k.a. Robert F. Kennedy Jr.’s son)? The two first stirred up an eventful summer fling in July 2012; they were spotted in Hyannisport, Massachusetts, getting cozy. A source told Us Weekly at the time, “Conor put his arm around Taylor and they kissed behind the boat shed.” A month later, Swift and Kennedy reportedly crashed his cousin’s wedding, a tale that Swift has since vehemently denied.

To thicken the plot even more, Taylor decided to buy a house on Cape Cod to be closer to Kennedy—a $4.9 million, 7-room summer home. According to the book The Kennedy Heirs, Kennedy ended his relationship with Swift in September 2012. “Conor liked Taylor, don’t get me wrong, but this business of her buying a house on the Cape made him nervous,” a friend of Conor’s told the biographer, J. Randy Taraborrelli. “It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy.” Swift sold the house shortly after.

Harry Styles (November 2012-January 2013)

Taylor Swift and Harry Styles walking in Central Park
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The tumult continued when Swift moved on from the American political heir and crossed the pond, sparking a relationship with British darling Harry Styles. The two first met at the 2012 Kids’ Choice Awards in March, but things didn’t take off until months later, when Swift, who was 22 at the time, was spotted wearing a silver paper plane necklace that appeared to belong to Styles, who was 18 at the time, in November of that year. A month later, they sent tongues wagging when they were spotted taking a romantic stroll through Central Park, which prompted the viral hashtag #Haylor. Weeks later, they rang in 2013 with a midnight kiss in Times Square following Swift’s performance on Dick Clark’s New Year’s Rockin’ Eve With Ryan Seacrest.

However, their coupling did not last long after their warm and fuzzy holiday season. The two took a trip to the British Virgin Islands in early January and reportedly got in a fight, which resulted in Swift leaving early—famously, alone on a boat, Entertainment Tonight reported.

Two years later, Swift released her fifth studio album, 1989, with songs “Out of the Woods,” “Style,” and “I Knew You Were Trouble,” which are all believed to be about the One Direction singer. Meanwhile, many speculate Styles’s tracks “Two Ghosts” and “Ever Since New York” off his self-titled debut album were inspired by Swift.

It appears the two have remained friendly over the years. Swift sweetly supported Styles’s win at the 2023 Grammys.

Calvin Harris (March 2015-May 2016)

Taylor Swift and Calvin Harris holding hands and walking
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Calvin Harris and Swift immediately felt the electricity upon being introduced by their mutual friend Ellie Goulding at the Elle Style Awards in February 2015. They started dating a month later and made their couple debut at the Billboard Music Awards in May of that year, sharing a public kiss at the ceremony. They celebrated their one-year anniversary with a tropical getaway and lots of PDA-packed pictures posted to Instagram in March 2016, and a month later, Swift even gushed she was “in a magical relationship” to Vogue.

However, after 15 blissful months (Swift’s first long-term public relationship), they called it quits—and things got a bit messy. Harris posted a string of aggressive tweets, now deleted, directed at Swift after the media reported she wrote the DJ’s smash single, “This Is What You Came For” (which was the one song they collaborated on). A year later, he told British GQ, per People, he regretted his behavior.

Tom Hiddleston (May-September 2016)

Tom Hiddleston and Taylor Swift walking together
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Tom Hiddleston first entered Swift’s orbit while she was still involved with Harris; the two met at the 2016 Met Gala in May. Swift moved on quickly from the Scottish DJ, becoming linked with the Marvel star the same month. In June of that year, they were seen kissing on a rock in Rhode Island and, a month later, enjoying some beach time, during which Hiddleston famously donned an “I ♥️ T.S.” tank top.

Their pairing ended up being just another summer fling, as it was over once September rolled around. Many speculated their relationship was a PR stunt, which the actor addressed during a February 2017 interview with GQ, saying, “Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time. Of course it was real.”

Joe Alwyn (May 2017-April 2023)

Taylor Swift and Joe Alwyn walking while holding hands
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Swift’s relationship with Joe Alwyn is her longest and most discreet to date—which many thought would end with a ring. Fans believe they first met at the 2016 Met Gala, while Swift was still an item with Harris, based off the lyrics in her song “Dress” from her sixth studio album, Reputation: “Flashback when you met me / Your buzz cut and my hair bleached / Even in my worst times / You could see the best of me.” They were each spotted at the same Kings of Leon concert and after-party at the Bowery Hotel in New York City in October 2016, but weren’t confirmed to be dating until May of the next year.

In a rare move, they put their love on display by sharing a public kiss at iHeartRadio’s Jingle Ball in N.Y.C in December. The couple managed to keep things close to their chests for a couple years, going largely publicly unspotted until the 2019 awards season, when they made their rounds together at the Golden Globes, BAFTAs, and Oscars. They continued strong into December 2020, when they put on a lovey-dovey display at the Golden Globes.

The same month, Swift released her ninth studio album, Evermore, which had fans speculating marriage between the two, based off her songs “Long Story Short” (which alludes to their sweet relationship) and “Willow” (for which Swift wore a wedding-style dress in the music video). Alwyn also contributed to songs “Champagne Problems,” “Coney Island,” and the title track under the alias William Bowery, as well as a few tracks on her eighth studio album, Folklore (which was released just months earlier). Swift ended up taking home Album of the Year for Folklore at the Grammys and gave Alwyn a sweet shoutout during her acceptance speech: “Joe, who is the first person that I play every single song that I write, and I had the best time writing songs with you in quarantine.”

Wedding rumors returned with the release of Swift’s song “Lavender Haze” off her 10th studio album, Midnights, in which she sings, “All they keep asking me is if I’m gonna be your bride / the only kinda girl they see is a one night or a wife.”

However union rumors were put to rest in April 2023, when it was confirmed the two split following six years of dating. A year later, in April 2024, Swift released TTPD with songs “So Long, London,” “Fresh Out the Slammer,” “Florida!!!,” “loml,” “I Can Do It With a Broken Heart,” and “How Did It End?” all speculated to be about Alwyn.

Matty Healy (May-June 2023)

Taylor Swift and Matty Healy walking together
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Swift caused quite the commotion when she mouthed “This one is about you. You know who you are. I love you,” on stage during her Eras Tour show in Nashville in May 2023, with Matty Healy in the audience—the same words he had mouthed two days before while performing with his band, the 1975. To fuel the rumor mill even more, they were spotted together on their way to Swift’s Nashville apartment the following day. They continued to hang out and were photographed leaving Electric Lady Studios in New York City together.

However, it seemed things ended just as they were getting started, as Entertainment Tonight confirmed they split at the beginning of June. “They are both extremely busy and realized they’re not really compatible with each other,” a source told the publication. Their short-lived romance appeared to take quite a toll on Swift, as several tracks off TTPD, including “Down Bad,” “I Can Fix Him (No Really I Can),” “Fortnight,” and “The Smallest Man Who Ever Lived” are rumored to be about the English musician.

Travis Kelce (July 2023-present)

Travis Kelce with his arm around Taylor Swift
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Swift and Travis Kelce romance was not on many people’s bingo’s cards, but they have since become one of the most talked about—and adored—star couples. The Kansas City Chiefs tight end shot his shot—although unsuccessfully—in the sweetest, most Taylor Swift-coded way: with a friendship bracelet. Kelce attempted to give Swift a beaded bracelet with his phone number on it at one of her Eras Tour shows in July 2023. Although he failed, one way or another, the news made it’s way to the hitmaker and she ended up contacting him directly. Once romance rumors started, they didn’t stop, until Kelce’s brother, Jason, confirmed they were in fact an item in September 2023.

What would follow was an exciting football season—that ended with a Super Bowl ring—with Swift consistently in the VIP stands, cheering on her man in Kansas City merch, mingling with his mom, Donna, and celebrating the team’s wins among her star-studded posse, including Blake Lively, Sophie Turner, and Ice Spice. Their relationship continued on strong into 2024 with PDA-filled moments, including an adorable on-stage shout out Swift gave Kelce in March by singing, “Karma is the guy on the Chiefs coming straight home to me,” replacing the original lyric “screen” to his football team. The same month, they enjoyed a couple’s getaway to the Bahamas, followed by a surprise appearance at Coachella and Patrick Mahomes’ charity gala in April.

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