Taylor Swift at the 2019 Billboard Women In Music

Taylor Swift Dating History: All The Guys Before Joe Alwyn

Home / Stars / Taylor Swift Dating History: All The Guys Before Joe Alwyn

By Kristin Myers on February 23, 2022 at 9:39 AM EST

Is Taylor Swift really engaged?

That's what fans have been asking! Rumors are swirling that she is engaged to actor Joe Alwyn. The two have been linked since 2016 and is Swift's longest relationship to date.

If the "Love Story" singer really is off the market, now is a perfect time to look back at all of the famous faces that helped inspire her infamous break-up songs!

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Joe Jonas (July 2008 - October 2008)

Joe jonas
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Taylor Swift dated Joe Jonas in July 2008, but their relationship didn't last long! On "The Ellen DeGeneres Show," Taylor revealed that he broke up with her through a 27-second phone call!

Although their romance was short-lived, he is rumored to have inspired many of her popular songs, including "Forever & Always," "Last Kiss," and "Better Than Revenge."

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Sophie Turner and Joe Jonas out and about
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In 2021, she released "Mr. Perfectly Fine" from "Fearless (Taylor's Version)", which many believe to be about their relationship as well. Jonas' current wife, "Game of Thrones" actress Sophie Turner, called the song a "bop."

The two have since cleared the air and it seems like there is no "Bad Blood" between them!

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Taylor Lautner (August 2009 - November 2009)

TAYLOR LAUTNER AT LAX
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Taylor met Taylor Lautner after they met on the set of the rom-com "Valentine's Day." Although the two once went to a hockey game together, the "You're Not Sorry" singer ended the relationship when she felt like it just wasn't going anywhere.

However, the song "Back to December" is widely believed to be about the "Twilight" star. At the 2010 American Music Awards, she sang "Back to December" live and followed it up with the lyrics from "Apologize" by One Republic. Taylor Lautner had made a parody video to that same song. Regardless, the two never reunited.

Taylor Lautner has since moved on and became engaged to nurse Taylor Dome, a close friend of the family, last November.

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John Mayer (November 2009 - February 2010)

John Mayer at the 55th Annual GRAMMY Awards
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After collaborating with John Mayer on "Half of My Heart," the two got together, but it wasn't for long.

Their relationship is rumored to have inspired many songs, including "Superman," "Ours," "The Story Of Us," "I Knew You Were Trouble," and "Dear John."

"Dear John" hints at a destructive relationship, with Taylor singing, "Don't you think nineteen is too young to be played by your dark twisted games when I loved you so?"

Jake Gyllenhaal (October 2010 - December 2010)

10th Annual LACMA ART FILM GALA Presented By Gucci
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Actor Jake Gyllenhaal recently suggested that artists "take responsibility" for their "unruly" fans, and he didn't have to name names for fans to know that he was talking about Taylor Swift.

Many of her "Red" songs, including, "We Are Never Ever Getting Back Together, "The Moment I Knew," "I Almost Do," and the ever-popular "All Too Well" are rumored to be about him. One of the problems with their relationship seemed to come down to their nine-year age gap.

At one point in the 10-minute version of the song, she sings, “You said if we had been closer in age / Maybe it would’ve been fine / And that made me want to die.” Later on, she sings, “And I was never good at tellin’ jokes, but the punch line goes / I’ll get older, but your lovers stay my age.”

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Gyllenhaal is currently 41 years old. His current girlfriend is model Jeanna Cadieu, 26. For reference, Swift is now 32.

Conor Kennedy (July 2012 - October 2012)

Conor Kennedy
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Reportedly, Taylor's relationship with Conor Kennedy ended due to the complications of dating long-distance after his mother passed away.

Taylor has confirmed that the song "Starlight" is about his grandparents, Robert and Ethel Kennedy. The song "Begin Again" is also rumored to have been inspired by Kennedy.

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Harry Styles (December 2012 - January 2013)

Harry Styles performs on the Today Show-NYC
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The relationship between former One Direction boy-bander Harry Styles and Taylor Swift didn't last for long. The relationship ended quickly after a heated argument during a vacation in the Caribbean, which caused Taylor to fly home.

In an interview with Elle, Taylor dished on their "very fragile" relationship.

"It felt very fragile, it felt very tentative," she recalled. "And it always felt like, 'Okay, what's the next roadblock? What's the next thing that's gonna deter this? How long do we have before this turns into just an awful mess and we break up?"

He is rumored to have inspired the songs "Out of the Woods," "I Know Places," "Clean, and "Style." The One Direction song "Perfect" is believed to be about Harry's relationship with Taylor.

Calvin Harris (March 2015 - June 2016)

Calvin Harris at The Brit Awards 2019 at the O2 Arena in London, UK.
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The "End Game" singer and Calvin Harris dated for 15 months. He is rumored to have inspired the song "I Did Something Bad" and "Getaway Car."

A friend close to the couple reportedly told PEOPLE the relationship ended because Harris was “intimidated” by Swift's success.

“[Harris] said on multiple occasions that he was intimidated by Taylor, which is why he would not attend any events where she was being honored, or any award shows unless he was nominated,” the friend said.

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Swift also co-wrote Harris' song "This Is What You Came For" until the pseudonym Nils Sjöberg. She originally didn't want to have their relationship overshadow the song, but Calvin didn't seem to be too happy when she revealed that she was one of the lyricists behind the track after they broke up. He went on a long Twitter rant accusing her of making him "look bad."

Tom Hiddleston (June 2016 - September 2016)

Tom Hiddleston Signs Autographs Outside Broadway Play "Betrayal"
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Taylor and "Avengers" actor Tom Hiddleston dated very briefly following her relationship with Calvin Harris. The song "Getaway Car" is also believed to be about her relationship with the Loki actor.

It is widely believed that their relationship ended due to the difficulty of maintaining a private relationship under intense public and media scrutiny.

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Joe Alwyn (October 2016 - present)

Joe Alwyn at the Tom Ford AW20 Show
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It's no secret that Taylor fell in love with Joe's "Gorgeous" blue eyes. The song "Delicate" is also rumored to be about their romance.

In 2018, Joe told British Vogue that “I’m aware people want to know about that side of things. I think we have been successfully very private, and that has now sunk in for people … but I really prefer to talk about work.”

When Taylor won Album of the Year at the 2021 Grammy Awards, Taylor thanked Joe by name, saying, “Joe, who is the first person that I sing every single song that I write.” She also said that she had “so much fun writing songs in quarantine with him.”

Taylor Swift hand-in-hand with boyfriend Joe Alwyn go on a long walk after lunch in NYC
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Fans who watched “Folklore: The Long Pond Studio Sessions” on Disney+ know that Joe actually worked with on multiple tracks for “folklore” and her follow-up album “evermore.”Writing under the pseudonym William Bowery, Joe helped create “betty” and “exile” on “folklore.” He also contributed to “champagne problems,” “coney island” and “evermore” from her “evermore” album.

Life & Style reported that the low-key couple actually got engaged on a three-day trip to Cornwall back in January. There were multiple reports at the time with rumors that she was engaged, but Life & Style waited until a month later to make the reveal.

But are the rumors true? Fans will just have to wait until Taylor or Joe confirm it to find out the truth!

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