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Taylor Swift’s boyfriends: From Joe Jonas to Matty Healy, pop diva’s many attempts to find love

Although Taylor Swift has been criticized for writing about her ex-boyfriends, let's be honest, her songs certainly are a vibe
UPDATED MAY 6, 2023
Taylor Swift has previously been linked with Joe Jonas and Matthew Healy (@joejonas/@taylorswift/Instagram, Francois Durand/Getty Images For Christian Dior)
Taylor Swift has previously been linked with Joe Jonas and Matthew Healy (@joejonas/@taylorswift/Instagram, Francois Durand/Getty Images For Christian Dior)

No one writes a breakup song better than Taylor Swift. The icon has been in several high-profile relationships over the years and has dated many prominent men in the entertainment industry, from musicians to actors. 

Although, the singer gets a lot of criticism for dating celebrities and then writing songs about them. But let's be honest, we wouldn't have some of Taylor's best lyrical work if she hadn't been open and honest about her romantic life and ex-boyfriends.

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A look at Taylor Swift's dating history 

The 'All too well' singer is notorious for sharing all of the highs and lows of each relationship in her lyrics, leaving fans guessing which ex-boyfriend the song was inspired from. Here's a look at Swift's dating history.

Matthew Healy (2023)

Matthew Healy attends the Christian Dior After Show Party at the the 30 avenue Montaigne Dior flagship store on June 24, 2022 in Paris, France.
Matthew Healy attends the Christian Dior After Show Party at the 30 Avenue Montaigne Dior flagship store on June 24, 2022, in Paris, France (Francois Durand/Getty Images For Christian Dior)

Swift was romantically linked to The 1975 vocalist Matthew Healy just weeks after her split from Alwyn made the news. In May 2023, a source told that the singers were in the "super-early" phases of dating but were already "madly in love" with each other, as per The Sun.

Joe Alwyn (2017-2023)

Taylor Swift, 32, and her British actor boyfriend, Joe Alwyn, 31 have reportedly been engaged secretly (Photo by Jackson Lee/GC Images)
Taylor Swift, 32, and her British actor boyfriend, Joe Alwyn, 31 have reportedly been engaged secretly (Jackson Lee/GC Images)

Swift found herself in her longest — and most secretive — relationship yet.  She and actor Joe Alwyn reportedly met at the 2017 Met Gala and began dating a few months later, though their romance was not widely publicized until the following year. “I was falling in love with someone who had a wonderfully normal, balanced life,” she said in her 2020 autobiographical documentary, 'Miss Americana', as per US Magazine.

“We decided together we wanted our relationship to be private. I was happy. But I wasn’t happy in the way I was trained to be happy. It was happiness without anyone else’s input. We were just happy," Swift wrote in one of the most romantic songs of all time for her then-lover boy Joe.



 

However, in April 2023, reporters claimed that Taylor and Joe's love story had ended, citing sources who said the separation was "not dramatic" and that "the relationship had simply run its course. That's why (Alwyn) hasn't been seen at any of her Eras Tour events," as per Vulture.

Tom Hiddleston (2016-2017)

tom hiddleston
Tom Hiddleston was linked with Taylor Swift (Gettyimages)

Following her breakup with Calvin Harris, Taylor reportedly began dating British actor Tom Hiddleston. Their relationship was highly publicized and lasted a few months, as per the US Magazine.

Calvin Harris (2015)

Recording artist Taylor Swift (R) hugs Calvin Harris at the iHeartRadio Music Awards which broadcasted live on TBS, TNT, AND TRUTV from The Forum on April 3, 2016 in Inglewood, California.
Taylor Swift hugs Calvin Harris at the iHeartRadio Music Awards (Jason Kempin/Getty Images for iHeartRadio / Turner)

After her split with Harry Styles, Taylor began dating Scottish DJ Calvin Harris in 2015. They had a relatively long relationship, lasting about a year and a half before breaking up in 2016, as per the source outlet.

Harry Styles (2012)

(FOR EDITORIAL USE ONLY) (L-R) Harry Styles and Taylor Swift speak during the 65th GRAMMY Awards at Crypto.com Arena on February 05, 2023 in Los Angeles, California.
Harry Styles and Taylor Swift speak during the 65th GRAMMY Awards (Frazer Harrison/Getty Images)

Taylor started dating One Direction member Harry Styles. Their relationship was highly publicized, and the two were often seen together in public. However, they ended up breaking up after a few months. Their relationship was dubbed as "Haytor" after Taylor was seen wearing Styles' silver airplane necklace, which she also wore in the video for their breakup song, 'Out of the Woods', as per the source outlet.



 

Conor Kennedy (2012)

Conor Kennedy attends HBO's
Conor Kennedy attends HBO's 'Ethel' New York Premiere at Time Warner Center on October 15, 2012, in New York City (Jason Kempin/Getty Images)

In 2012, Taylor dated Conor Kennedy, the grandson of Robert F Kennedy, Jr. The relationship was brief, and the two amicably split, as per the Sun.

Jake Gyllenhaal (2010)

Jake Gyllenhaal attends the 94th Annual Academy Awards at Hollywood and Highland on March 27, 2022 in Hollywood, California.
Taylor Swift's 'All Too Well' was speculated to be written about Jake Gyllenhaal (Mike Coppola/Getty Images)

Taylor sparked dating rumors with Jake Gyllenhaal in 2010 after US Weekly covered a story about them in December of that year. Fast-forward to January, the magazine reported that the couple had broken up. 'All Too Well' is widely assumed to be about Swift's 2010-2011 relationship with Jake Gyllenhaal. They started dating when she was 19 and he was 28. Was this ever confirmed? No, but that hasn't stopped fans from deciphering the additional lyrics, which support the notion that 'All Too Well' was inspired by the breakup with Jake.



 

John Mayer (2009)

Musicians John Mayer (L) and Taylor Swift attend the launch of VEVO, the world's premiere destination for premium music video and entertainment at Skylight Studio on December 8, 2009 in New York City.
Musicians John Mayer (L) and Taylor Swift attend the launch of VEVO, the world's premiere destination for premium music video and entertainment at Skylight Studio on December 8, 2009, in New York City (Dimitrios Kambouris/Getty Images for VEVO)

In 2010, Taylor reportedly began dating musician John Mayer, who is known for dating many famous women. Their relationship was highly publicized and ended after a few months. Once again, Taylor's heartbreak led to some of her most famous songs, including 'Dear John', which was rumored to be about Mayer, as per the source outlet.



 

Taylor Lautner (2009)

Actor Taylor Lautner attends GREY GOOSE Pre-Oscar Party hosted by Michael Sugar, Doug Wald, Nathan Kahane and Warren Zavala at Chateau Marmont on February 23, 2013 in Los Angeles, California.
Taylors Lautner reportedly met the singer on the set of the movie 'Valentine's Day' (Alexandra Wyman/Getty Images for Grey Goose Vodka)

After her brief relationship with Joe Jonas, Taylor started dating actor Taylor Lautner in 2009. The two Taylors met on the set of the movie 'Valentine's Day' and dated for a few months before reportedly calling it quits, as per the source outlet.



 

She allegedly wrote 'Back to December' for him, and when asked what he thought of the song in 2016, Twilight Taylor said, “That’s what she does," as per US Magazine.

Joe Jonas (2008)



 

One of her earliest known relationships was with musician Joe Jonas in 2008 when they were both teenagers. Their relationship only lasted a few months, but it ended up inspiring some of Taylor's most famous songs, including 'Forever and Always', 'Better Than Revenge' and 'Mr Perfectly Fine'. In an interview with Ellen in November 2009, Taylor said, “When I find that person who 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.”



 

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