A breakdown of Taylor Swift’s dating history

Taylor Swift just dropped the rerelease of her 2012 album “Red,” which was allegedly inspired by her short-lived romance with Jake Gyllenhaal. 

The actor quickly started trending on Twitter over the weekend, especially after the singer released her 10-minute updated version of “All Too Well,” which featured lyrics such as: “They say all’s well that ends well/ But I’m in a new hell every time you double-cross my mind/ You said if we had been closer in age maybe it would have been fine/ And that made me want to die.” She even sang the rumored Gyllenhaal breakup song on “SNL.”

Swift has won multiple Grammys for songs and albums inspired by her past relationships, so let’s break down her dating history and how she found love with her current boyfriend Joe Alwyn. 

Joe Jonas

Swift and Jonas dated from July 2008 to October 2008.
(Jeff Kravitz/FilmMagic)

Swift and Jonas dated from July 2008 to October 2008 after he reportedly called it off with a 27-second phone call. 

He allegedly inspired the songs “Last Kiss” on her album “Speak Now ” and “Forever and Always” on “Fearless.”

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Lucas Till

The actor and singer dated in 2009.

The actor and singer dated in 2009.
(Presley Ann/Getty Images for 3rd Base)

The actor and singer dated in 2009 after meeting on the set of Swift’s music video for “You Belong With Me.”

Till actually spoke about the relationship with MTV back in the day. “We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other,” he said. 

“[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,” Till explained.

Taylor Lautner

Swift and "Twilight’" star Taylor Lautner dated in fall 2009. 

Swift and “Twilight’” star Taylor Lautner dated in fall 2009. 
(Jean Baptiste Lacroix/WireImage)

Swift and the “Twilight” star dated in fall 2009. They co-starred in the movie “Valentine’s Day.” Lautner supposedly inspired the songBack to December.”

John Mayer

John Mayer and Taylor Swift briefly dated from December 2009 to February 2010.

John Mayer and Taylor Swift briefly dated from December 2009 to February 2010.
(Dimitrios Kambouris/Getty Images for VEVO)

The two musicians briefly dated from December 2009 to February 2010 after collaborating on the song, “Half of My Heart.” 

The songs “Dear John,” “Ours” and “I Knew You Were Trouble” are rumored to be about Mayer. 

Mayer reacted to the “Dear John” lyrics in an interview with Rolling Stone. He said, “I never got an email. I never got a phone call. I was really caught off guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”

Jake Gyllenhaal

Fans widely believe Taylor Swift's "All Too Well" is about the actor Jake Gyllenhaal.

Fans widely believe Taylor Swift’s “All Too Well” is about the actor Jake Gyllenhaal.
(Getty Images)

The former couple dated from October 2010 to January 2011. Many songs on Swift’s 2012 album “Red” were allegedly about him.

Fans have always been particularly interested in Swift singing about leaving a red scarf at Jake’s famous sister, Maggie’s, house and never getting it back. 

TAYLOR SWIFT SINGS RUMORED JAKE GYLLENHAAL BREAKUP SONG ‘ALL TOO WELL’ ON ‘SNL’

Conor Kennedy

Swift and Conor Kennedy, the grandson of Robert F. Kennedy dated between July 2012 and October 2012.

Swift and Conor Kennedy, the grandson of Robert F. Kennedy dated between July 2012 and October 2012.
(Photo by Taylor Hill/WireImage)

Swift and the grandson of Robert F. Kennedy dated between July 2012 and October 2012. They were photographed together in Hyannisport, Massachusetts. 

He reportedly was the inspiration behind the song “Begin Again.”

Harry Styles

Taylor Swift and Harry Styles dated from November 2012 to January 2013.

Taylor Swift and Harry Styles dated from November 2012 to January 2013.
(David Krieger/Bauer-Griffin/GC Images)

The two singers dated from November 2012 to January 2013 and he was Swift’s source of inspiration for “Out of the Woods” and “Style.”

Calvin Harris

Swift and the DJ Calvin Harris  dated from February 2015 to May 2016.

Swift and the DJ Calvin Harris  dated from February 2015 to May 2016.
(Raymond Hall/GC Images)

Swift and the DJ dated from February 2015 to May 2016 and went public at the 2015 Billboard Music Awards. 

The songs “I Did Something Bad” and “Getaway Car” are supposedly about him. 

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Tom Hiddleston

The Marvel star Tom Hiddleston and Taylor Swift dated briefly from May 2016 to September 2016 

The Marvel star Tom Hiddleston and Taylor Swift dated briefly from May 2016 to September 2016 
( Cameron Richardson/Newspix/Getty Images)

The Marvel star and Swift dated briefly from May 2016 to September 2016 as they jetted around the world from England to Australia. They met at the 2016 Met Gala. 

“Getaway Car” is allegedly about Hiddleston. 

Joe Alwyn

Swift and Joe Alwyn have been dating since May 2017.

Swift and Joe Alwyn have been dating since May 2017.
(Jackson Lee/GC Images)

Swift and Alwyn have been dating since May 2017. In her 2020 documentary, “Miss Americana,” Swift recalls falling for the English actor. “I also was falling in love with someone who had a wonderfully normal, balanced life,” she said. “We decided together we wanted our relationship to be private.”

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They rarely make public comments about each other but her 2019 album “Lover” was inspired by him and they even wrote songs together (“Betty” and “Exile”) on her 2021 album “folklore” under the pseudonym “William Bowery.”

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