From Harry Styles to John Mayer: Taylor Swift's Dating History


| LAST UPDATE 09/28/2023

By Abby Wall

Swift has dated some of Hollywood's finest, that's for sure! The Gorgeous singer is known for turning her relationships into song, but what do her exes have to say about it? Let's take a closer look.

Dating Reputation

People might give Taylor Swift the side eye for dating celebs and then writing songs about them, but the truth is her fans love it. Her honesty is refreshing, and people can actually relate to what she's feeling!

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No wonder her most recent tour has grossed hundreds of millions of dollars! Besides being recognized as one of the most beloved musicians in the world, the Grammy award-winning artist has racked up quite the dating resume over the past decade, so let's just dive right in and take a closer look.

Joe Jonas

Let's take things back to the summer of 2008. The Jonas Brothers made their movie debut with Camp Rock, they're featured on the cover of Rolling Stones, and they had just released their third studio album, A Little Bit Longer. So basically, they were living the dream.

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Jeff Kravitz / Contributor via Getty Images

So, when news broke that Joe Jonas was dating Taylor Swift, audiences everywhere welcomed the ideal pop duo. Swift was only 18 at the time, and they dated for three months before their relationship came to an end. However, it still managed to be one of the songstress's most memorable relationships to date.

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The 27-Second Breakup Call

According to the Bad Blood singer, the Disney star ended their relationship with a 27-second phone call. "That's got to be a record," she told Ellen DeGeneres. When I find the person who's right for me, he'll be wonderful. I'm not even going to remember the boy who broke up with me over the phone," she added.

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TheEllenShow via YouTube

That same year, Swift released the song, Forever and Always, inspired by her ex, singing, "Was I out of line? / Did I say something way too honest, made you run and hide / Like a scared little boy." However, it's water under the bridge now, as she has since apologized for calling him out like that!

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Lucas Till

Following her relationship with Jonas, Swift briefly dated the Son of the South star, Lucas Till. Lucas actually starred in Swift's 2009 music video for the iconic song, You Belong With Me and apparently began dating shortly after for just a little bit.

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Alberto Terenghi/IPA/Shutterstock

However, Till told MTV, "There was no friction because we were too nice," adding, "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 didn't work out."

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Taylor Lautner

Taylor and Taylor! Everyone loved the idea of Taylor squared, but unfortunately, it didn't last long. (Although Taylor Lautner did end up marrying another Taylor). Anyways, Lautner and Swift dated for three months back in 2009 when the couple were filming the iconic film Valentine's Day.

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But a source told Us that "there was no chemistry" between the couple and that "it wasn't really developing into anything." So, "they decided they were better as friends." After their breakup, Swift released Back to December - allegedly about Lautner. When he was asked about the song, Lautner just said, "That's what she does."

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I Can See You

The two really were better off as friends, as they actually maintained a really great relationship! Audiences were shocked when Swift re-released the song, I Can See You and cast a certain ex-boyfriend as one of the main faces. That's right, Taylor Lautner himself!

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Chelsea Lauren/Shutterstock

Swift explained that Lautner was a "very positive force in my life when I was making the Speak Now album," so it only made sense! The songstress further explained that "He and his wife have become some of my closest friends, and it's very convenient because we all share the same first name." Love it.

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John Mayer

No one in the history of pop culture will ever forget this relationship! The duo first collaborated on Mayer's single Half of My Heart back in 2009 after Mayer himself tweeted that he would want to sing with Swift herself. The couple later performed White Horse and Your Body Is a Wonderland together, and the romance rumors began.

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Chelsea Lauren/Shutterstock

Following their single together, Mayer began to sing Swift's praises, calling her the "world's biggest star" to Access Hollywood. "I'm a huge fan, and I think she's got a really great voice," he told Ellen DeGeneres, saying, "She's one of the smartest, most talented people around right now. I think she's that genuine."

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Dear John

By the beginning of 2010, Mayer and Swift were spotted in Nashville, leaving the public to question whether they were more than just friends. Swift, only 19 at the time, and John, 12 years her senior, never officially announced they were together, but things clearly went south when Swift released Dear John in October of that year.

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Amanda Schwab/Starpix/Shutterstock

Per the name of the song, fans believe it to be about her breakup with the Gravity singer. Fans also pointed out specific lyrics to the song that all point towards a certain someone. "Don't you think nineteen is too young/ To be played by your dark twisted games / When I loved you so?" she sings.

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Battle of the Songs

Mayer was less than impressed with his ex's breakup song, telling Rolling Stone that the lyrics made him "feel terrible." He told the publication, "Because I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do."

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Although he referred to her writing methods as "cheap songwriting," Mayer later released Paper Doll a year later, which fans speculated was a response to Taylor's Dear John. The lyrics reference a red scarf, the number 22 after her hit single, and a direct response to a line from Swift's song.

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Hardcore Swifties

Once Swift released the re-recording of her album Red in 2021, the record reignited speculation about a few of her past romances, including Mayer. According to Page Six, Mayer even began receiving death threats from some of Swift's most die-hard fans. In response, Swift asked her fans to practice "kindness" and "gentleness."

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John Angelillo/UPI/Shutterstock

"I'm 33 years old; I don't care about anything that happened to me when I was 19 except the songs I wrote," she explained. "So what I'm trying to tell you is that I am not putting this album out, so you should feel the need to defend me on the internet against someone you think I wrote a song about 14 million years ago."

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Cory Monteith

So even though Mayer might not have been the one for Swift, it doesn't mean that Taylor tapped herself out of the game! In fact, just a few weeks after calling things quit with Hollywoods Casanova, the Cruel Summer singer was spotted hanging with a Glee star.

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Rick Diamond / Staff via Getty Images

In March of 2010, Swift and Cory Monteith were seen having a fun night out bowling in Los Angeles, and according to an inside source, "they seemed really happy." Monteith might have manifested that moment as he once told Us that she was his celebrity crush. The actor tragically passed away in 2013.

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Jake Gyllenhaal

By the Fall of 2010, Swift had linked up with superstar Jake Gyllenhaal and well, the tabloids were on it! Photos of them strolling the park in NYC were released, and the whole world was fascinated by the pairing. However, things didn't last too long...

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After a two-month fling, a source told Us that Jake broke up with Taylor out of the blue. "It was a 180-degree turn, and so out of the blue," the source said, "Jake just told her it wasn't working out.…Taylor is really upset and hurt. She doesn't know what she did for him to put a stop to it. She feels really burned by him."

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All Too Well

It does sound like they had a pretty amicable breakup, but in true Swift fashion, a few songs on the Musicians 2013 album, Red, were thanks to Gyllenhaal. The most famous song in question, however, was All Too Well, which she later admitted to writing after feeling like "a broken human."

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Years later, Swift released the extended version of All Too Well with an accompanying music video that really got people talking. After adding in new lyrics, fans were almost certain the track was about Gyllenhaal. However, the actor told Esquire, "It has nothing to do with me," he said. "It's about her relationship with her fans."

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Chord Overstreet

After the world was invested in Swift and Gyllenhaal's short-term relationship, fans were saddened to hear of the breakup news but, of course, wondered who Taylor would date next! As it turned out, she was also just looking for a brief fling when she met Chord Overstreet.

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Chord Overstreet, best known for his role as Sam Evans on Glee, briefly hung out with Swift back in 2011. An insider revealed to Us that the Blank Space singer "reached out to Chord," and together, they went out to an L.A. Kings game. At the time, the insider shared he was "into her," but things were casual.

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Adam Young

Adam Young stole Taylor Swift's heart, and in response, he got a love song! Although the details of the couple's relationship are not so clear, it turns out they exchanged emails at one point (how 2000s) and then went out a few times.

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Joseph Okpako / Contributor via Getty Images

Young apparently wrote a love song dedicated to Swift on Valentine's Day, singing, "Everything about you is beautiful" and "You are a true princess from a dreamy fairy tale." The songstress later came out with the song, Enchanted, which fans seem to think is about Young.

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Eddie Redmayne

In 2012, The Good Nurse actor was spotted flirting it up with the songstress, causing some buzz to stir around the potential fling with the artists. Apparently, they met when they were auditioning for the film adaptation of Les Miserables, and the rest was history.

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The couple enjoyed a brief fling, but when Swift didn't land the role of Eponine, sources said Redmayne didn't want to commit to a long-distance relationship. Swift was only 22 at the time but would soon date American royalty and actually live out her fairytale fantasies!

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Conor Kennedy

That's right! Swift started dating Robert F. Kennedy's then-18-year-old grandson Conor back in 2012. The couple was photographed getting cozy in Hyannisport, Massachusetts, with news saying, "Connor put his arm around Taylor, and they kissed behind the boat shed."

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However, things unfortunately didn't last all too long, but not to fret; apparently, it was all good! According to E!, the split was "totally amicable and down to the distance between them." What a bummer, though; Taylor Kennedy has a nice ring to it...

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Harry Styles

And then there was Harry Styles. Romance rumors took over the world when Swift was spotted wearing Harry's silver airplane necklace. What makes more sense than a One Direction member and popstar icon Taylor Swift dating? Nothing really. By December 2012, the couple went public after being spotted at the Central Park Zoo.

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David Fisher/Shutterstock

However, things didn't last too long for these lovebirds, and apparently, a fight during the holiday szn led to a breakup in January 2013. However, the couple seem to be on solid terms, and at the end of the day, Swifties have the breakup to thank for basically the entire 1989 album.

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Thanks, Harry

1989 ended up being one of Swift's most successful albums thanks to a certain British popstar! Fans are certain the songs, I Knew You Were Trouble and Style, are about her ex, plus the singer even rocked that airplane necklace in her music video for Out of the Woods.

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Frazer Harrison / Staff via Getty Images

However, Styles has always kept things cute! Following a performance of I Knew You Were Trouble at the 2013 Brit Awards, the Watermelon Sugar singer told Us Weekly that her performance was "great" and that "she always puts on a good show." Good to know they're on good terms!

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Taylor’s Inspo

As we know, Taylor is true and constant in using her relationships and breakups as a source of inspiration for her music. However, in most cases, she keeps the details of a song on the low. However, Taylor's fans are pretty good at dissecting her music to figure out which song is about which ex!

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For example, when People asked her the inspiration for the song Dear John, Swift kept it tight-lipped. Without giving away who it was about, she explained to PEOPLE that the song was "a tough one to write." The Grammy winner explains writing these songs is her way of saying everything she wishes she could have said at one point.

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Calvin Harris

After dating Styles, the singer began dating Scottish DJ Calvin Harris. The couple was introduced to one another at the 2015 Brit Awards through Ellie Goulding and made it Instagram official shortly after. The duo kept things lowkey, but on various occasions, they were seen locking lips and thriving as a couple.

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James Devaney / Contributor via Getty Images

Taylor told Vogue in April 2016, “I'm in a magical relationship right now. And of course, I want it to be ours, and low-key," adding, "This is the one thing that's been mine about my personal life." However, the couple eventually called it quits after 15 months together, but it was a messy ending...

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This Is What You Came For

Right before the breakup, Harris released the hit single This Is What You Came For, which was co-written by Nils Sjöberg, an unknown individual. However, following the couple's breakup, it was revealed to be a pseudonym for Swift. But at the time of the song's release, no one knew! And well, Harris was not happy once the news broke.

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The DJ lashed out on X, writing, "I figure if you're happy in your new relationship, you should focus on that instead of trying to tear your ex-bf down for something to do." He did give Swift credit where it was due, but he said he did most of the work. "I wrote the music, produced the song, arranged it, and cut the vocals."

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Look What You Made Me Do

Calvin continued to share that Taylor initially "wanted it kept secret, hence the pseudonym," but news eventually broke that Nils was actually Swift. The tweets were deleted shortly thereafter, but fans were waiting for what would eventually become Taylor's breakup song, Look What You Made Me Do.

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In the rebuttal music video, audiences spotted a tombstone bearing the name Nils Sjöberg. Owch. Years later, when Swift released Midnights, fans theorized the track High Infidelity was about Harris. This is because it included the date April 29, the day This Is What You Came For debuted in 2016.

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Tom Hiddleston

Just two weeks following her breakup with Harris, news broke that Swift was right back on the dating wagon. This time, she had been spotted kissing the Loki actor, Tom Hiddleston. "They were all over each other — hugging and kissing — even though there were 20 people coming and going on the beach," an eyewitness told The Sun.

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"They looked like any young couple madly in love without a care in the world." However, three months later, Hiddleswift was over, but the actor had nothing but great things to say about his ex. "Taylor is an amazing woman," he told GQ in 2017. "She's generous and kind and lovely, and we had the best time."

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Joe Alwyn

Following the singer's brief stint with Hiddleston, Swift fell into her longest relationship yet with British actor Joe Alwyn, but after six years of dating, the couple called it quits. But where exactly does this love story start? Apparently, on the first Monday in May!

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Jackson Lee / Contributor via Getty Images

You know what that means - the 2016 Met Gala! Although it was never confirmed, Taylor's song Dress, where she sings, "Flashback to when you met me / Your buzz cut / And my hair bleached," implies that was the night. The then-27-year-old kept things under wraps but by 2018 their relationship was Instagram official!

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Keeping Things Private

Although they were rarely spotted together, the couple was seen here and there, looking madly in love at award shows, concerts, or intimate dinner dates. Swift later explained to The Guardian that she decided to keep her relationship private in order to keep a boundary between her working and personal life.

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Cindy Barrymore/Shutterstock

"I've learned that if I do, people think it's up for discussion, and our relationship isn't up for discussion," she said. "That's where the boundary is, and that's where my life has become manageable. I really want to keep it feeling manageable." She still looped in her fans through her music, though.

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The Real Deal

The tabloids were calling their relationship "the real deal," and Swifties were thrilled for their queen that she had finally found the one. In 2019, an insider to Us that "Taylor's friends are all talking about a proposal and how she really wants to marry Joe" and that "he's her dream guy."

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Robert Kamau / Contributor via Getty Images

Another source explained that the couple at that point had "discussed children" and that the singer was "very excited about that chapter of her life when the timing is right." Fans even got a glimpse at their loving relationship in Taylor's 2020 documentary, Miss Americana.

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The Breakup

However, as Swift embarked on her Eras tour, Joe was nowhere to be seen. An insider revealed to PEOPLE that the couple decided to call things off due to "differences in their personalities." The source explained that they "weren't the right fit for one another." Apparently, he struggled with "Taylor's level of fame."

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"They had plenty in common and fell in love in a safe bubble while she was retreating from the world during Reputation," the source said. "Then, the pandemic hit, and they were locked down together and able to continue growing their relationship in this insulated way. But he didn't really 'know' her yet outside of that bubble."

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Matty Healy

But Taylor wasn't going to let Joe bring her down! In fact, shortly after their breakup, rumors started flying all over town that she had been casually seeing The 1975 frontman, Matty Healy. Apparently, the two hung out back in 2014, when they met backstage at one of his concerts, and the two hit it off.

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David M. Benett / Contributor via Getty Images

Healy was then spotted wearing a 1989 album T-shirt, following Taylor to wear The 1975 shirt. The singer was seen at Swifts Eras Tour in Nashville, with a source explaining they are "having a good time reconnecting again." However, after just a month, reports explained the two "had fun together, but it was never serious.”

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Who Was Next?

"I promise that you'll never find another like me," Taylor sings in the hit song Me! And, well, her exes would probably agree! Since she was a teenager, Swift's romantic relationships have been under watch, but Taylor has always been able to maintain boundaries between her private life and professional life.

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Alwyn once said in an interview with The Sunday Times that he finds it "flattering" he is the inspiration behind Swift's music, but would all her exes agree? Depending on how the relationship pans out, Taylor's exes have all been the subject of one song or another, but who was going to be next?

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Travis Kelce Rumors

It doesn't look like fans will be kept waiting too long for that question to be answered. We've been hearing rumors of a fresh romance between Tay and none other than Kansas City Chiefs tight end Travis Kelce! So, what exactly is the tea here, and what do we know for sure so far?

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Michael Owens / Contributor via Getty Images

Taylor was in the crowd at the Chiefs vs Jets game, sitting next to Kelce's mom and cheering the red team on. She later had her arm around him at the postgame party, where the pair "showed up together and were cute and normal, just hanging out and chatting," PEOPLE reported. Stay tuned as we find out what's next for these two…

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