A Look Back at Taylor Swift's Long List of Ex-Lovers

Anna Quintana - Author
By

Jun. 5 2023, Updated 8:03 p.m. ET

Side-by-side photos of Joe Jonas, Taylor Lautner, Calvin Harris, Tom Hiddleston
Source: Getty Images

It's no secret Taylor Swift's music is full of Easter eggs from past relationships.

From the good ("Lover"), the bad ("All Too Well"), and the ugly ("Dear John"), Taylor has used her exes as inspiration for her songs, and we don't blame her.

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Most recently, Taylor split from Matty Healy. Before that, Taylor split from her longtime boyfriend Joe Alwyn. The breakups promoted us to take a walk down memory lane, because as Taylor said, she has a long list of ex-lovers, and it can be hard to keep track.

Sam Armstrong (2006)

In 2018, Sam Armstrong jumped on a Twitter thread that asked, "Who is the most famous alum of your high school?" He replied, "Taylor Swift. What if I told you I dated her? True story." He also shared a photo of the couple in high school.

It wasn't long before Taylor's fans outed him for reportedly cheating on the singer, and being the inspiration for her song, "Should've Said No" from her debut album.

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Joe Jonas (2008)

Joe Jonas performing in 2008
Source: Getty Images

Taylor and Joe Jonas only dated for three months in 2008, but their relationship made headlines after Taylor went on The Ellen DeGeneres Show and claimed that Joe broke up with her on a 25-second phone call.

Joe denied Taylor's story, writing on MySpace, "A phone call can be pretty short when someone else ends the call." Taylor eventually apologized to Joe and they are now friends, but we will always have "Forever & Always."

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Lucas Till (2009)

After appearing in Taylor's music video for "You Belong With Me," Lucas briefly dated the then-country singer. However, their relationship was brief.

"We dated for a little bit. But, there was no friction because we were too nice," he told MTV News in 2009. He explained, "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."

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Taylor Lautner (2009)

Taylor Lautner and Taylor Swift at the 2009 VMAs.
Source: Getty Images

Taylor and Taylor met on the set of Valentine's Day in July 2009 and instantly became young Hollywood's It couple. Dubbed "Taylor Squared" by fans, the Twilight actor and singer attended the MTV Video Music Awards together in September 2009, but their relationship would end shortly after in December 2009.

Cue "Back to December."

However, they remained good friends, with Taylor (Swift) telling Glamour in 2010, "He's one of my best friends. He's wonderful, and we'll always be close. I'm so thankful for that." As for Taylor (Lautner) he has since married another Taylor (Dome).

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John Mayer (2009)

John Mayer and Taylor Swift performing at  Z100's Jingle Ball in December 2009.
Source: Getty Images

Taylor quickly rebounded with John Mayer — and came to regret her fling with the notorious bachelor if her song "Dear John" is any indication. John responded with a song of his own ("Paper Doll").

Fast forward, and John told the audience during his concert in April 2023 that the song is "a little bitchy."

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Cory Monteith (2010)

Taylor Swift and Cory Monteith
Source: Getty Images

Although Taylor never confirmed her relationship with the Glee actor, it's rumored that her song "Mine" is about Cory Monteith. Following his tragic death in 2013, Taylor tweeted, "Speechless. And for the worst reason."

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Jake Gyllenhaal (2010–2011)

Jake Gyllenhaal in 2011
Source: Getty Images

Oh, Jake.

Taylor penned her song "All Too Well" about her relationship with the "Donnie Darko" actor, who is 10 years her senior after their split in 2011. She has since re-recorded the song and released a 10-minute version along with a short film of the song — prompting many to wonder if he still has her red scarf.

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Conor Kennedy (2012)

Conor Kennedy in 2019
Source: Getty Images

American royalty met pop royalty when Taylor began dating Conor Kennedy, the grandson of Robert F. Kennedy. Before their breakup, Taylor even purchased a home near the Kennedy compound in Hyannis Port. As expected, she no longer owns the home.

It's rumored that her song, "Begin Again" is about Conor.

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Harry Styles (2012–2013)

Taylor Swift and Harry Styles at the Grammy Awards in 2023
Source: Getty Images

Harry and Taylor might have only dated for a month between 2012 and 2013, but their short relationship provided Taylor with more than enough lyrical inspiration.

Her songs "I Knew You Were Trouble," "Out Of The Woods," and "Style" are said to be about the British singer. In 2023, Harry and Taylor reconnected at the Grammy Awards and it looked like there were no hard feelings between the two.

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Calvin Harris (2015–2016)

Calvin Harris on the red carpet and him giving Taylor Swift a hug
Source: Getty Images

Calvin Harris (or should we say Adam Wiles) and Taylor went Instagram official in June 2015, but one year later, the couple calls it quits.

"The only truth is that a relationship came to an end & what remains is a huge amount of love and respect," Calvin tweeted at the time. However, things quickly turn nasty when it was revealed that Taylor has already moved on with Tom Hiddleston.

So, it is no surprise that Taylor's 2017 album Reputation is full of rumored digs at Calvin, including her song "Dancing With Our Hands Tied."

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Tom Hiddleston (2016)

Tom Hiddleston and Taylor Swift at the 2016 Met Gala.
Source: Getty Images

Who can forget Tom's "I Heart T.S." shirt? The couple met at the May 2016 Met Gala and had a whirlwind romance that took them from her home in Rhode Island to the U.K. and Rome in just three months.

However, the couple split in September 2016. By 2017, Swifties had flagged "Getaway Car" as Taylor's ode to her relationship with Tom.

"Taylor is an amazing woman,” he told GQ in 2017. "She’s generous and kind and lovely, and we had the best time... A relationship in the limelight… A relationship always takes work. A relationship in the limelight takes work. And it’s not just the limelight. It’s everything else."

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Joe Alwyn (2017–2023)

Taylor Swift and Joe Alwyn
Source: Getty Images

After six years together, Taylor and Joe Alwyn split in April 2023. In what was her longest (and most private) relationship, Taylor is said to have penned a handful of songs about the British actor, who even collaborated with Taylor using the pen name William Bowery on her Folklore album.

Those songs include "End Game," "King of My Heart," and "Lover."

As to why they broke up, a source told People their split was caused by "differences in their personalities."

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Matty Healy (2023)

Matty Healy performs on stage at Lollapalooza Chile 2023, drinking from a bottle and smoking a cigarette
Source: Getty Images

When the news about Taylor and The 1975's Matty Healy broke, the Internet immediately became obsessed. After six years of Taylor being off the market, the world had forgotten what it was like to see her name in the headlines next to a new beau.

The Taylor and Matty dating rumors weren't necessarily new, though. Fans had speculated about them before back in 2013. It was never fully confirmed if they were truly dating. However, they both wore the other's merch out in public.

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Every so often the rumors would resurface since they remained friends. In 2016, Matty shut down the rumors. Controversially, he told NME that being seen as just Taylor's boyfriend would feel "emasculating." Over the years, fans would bring this comment back up as just one note in a laundry list of qualms with the musician.

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Matty is known for his satirical performances and, oftentimes, offensive statements. As a result, when Taylor was formally linked to him in April 2023, many fans didn't like the mix. Matty attended multiple dates of her sold-out Eras Tour and was photographed by her side multiple times.

However, on June 5, 2023, TMZ reported that the pair had broken up.

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Along the way, Taylor has been linked to more famous men, but their relationship status was never confirmed, or they denied dating. They include:

  • Stephen Barker Liles (2008)
  • Adam Young (2011)
  • Chord Overstreet (2011)
  • Eddie Redmayne (2012)
  • Zac Efron (2012)
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