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Taylor Swift boyfriends

To learn about Taylor's current boyfriend, please read Current love interest.

Taylor Swift has stated that she has written songs about all of her ex-boyfriends. This is a list of who is rumored to be the inspiration for which songs, and brief summaries of each relationship. Some of these might be fan conclusions as Swift has never publicly confirmed the majority of them.

Boyfriends

Drew Dunlap

The song “Tim McGraw was inspired by Drew, her ex-boyfriend. Their relationship ended because he had to go to college. Taylor told USA Today, "He bought the debut album Taylor Swift and said he really loved it, which is sweet. His current girlfriend isn't too pleased with it, though." He was going away to college so she wanted to write him something to remember her goodbye.

Jordan Alford

Picture to Burn” was written about him, whom she calls a "redneck heartbreak who's really bad at lying", and says he never let her drive his pick-up truck. According to Taylor, Alford thought she was "obsessive and crazy", and was now out to tell everyone about this.

Drew Hardwick (not an ex)

Teardrops on My Guitar” was written about a boy she liked, whom she never actually dated. "Drew was a real person!" she tells. Drew was surprised when he heard his name in the song. "I never knew she liked me," Drew says. Taylor stated that two years after the song came out Drew showed up at her house and asked her on a date. She declined. "It was the perfect fairytale ending but a little too late."

Sam Armstrong

Sam cheated on Taylor, and in response, she wrote: "Should've Said No". In the CD booklet for her debut album, Taylor Swift, every S, A, and M was capitalized if it was in the correct order. Sam is currently on Twitter and actively writes hate posts about Taylor.

Joe Jonas

Joe broke up with her over a 27-second phone call, which is something she has complained about on The Ellen DeGeneres' Show. She got her record company to let her record a song about it, to add at the last minute to her album. “Forever & Always” is the name of that song. She also wrote, “Last Kiss” about him, and “Better Than Revenge” is about his ex-girlfriend, Camila Belle. The previously unreleased song "Mr. Perfectly Fine", from the re-recorded version of Fearless, is also rumored to be about him. "Holy Ground" from her 4th album Red is rumored to be a callback to Taylor's relationship with him.

Taylor Lautner

Taylor Lautner became her boyfriend after they met on set for the film Valentine's Day. Their relationship was popularly known as Taylor Squared. They broke up in early 2010. She mentioned going to a hockey game with him during her October 29th, 2009 appearance on The Ellen Show. According to MTV he was more into her than she was into him, him going everywhere he could see her, but it was not working out. [1] The song “Back to December” is suspected to be about him as an apology. Some of the lyrics go, "You gave me roses, and I left them there to die... So this is me swallowing my pride, standing in front of you saying I'm sorry for that night... You gave me all your love and all I gave you was goodbye." At the end of the song, she asks for his forgiveness and hints at the fact she wants to be with him again. The couple hasn't reunited. At the 2010 American Music Awards, Swift performed the song and at the end added, "and he said... it's too late to apologize" from the popular song "Apologize" by the band One Republic.[2] She is alluding to the parody video Taylor Lautner made for "Apologize". [3] Time magazine listed this as one of the top apologies of 2010. [4] They were able to stay friends and in 2023 he appeared in the music video for I Can See You.

John Mayer

The songs “Dear John”, "Ours", "Superman", "The Story of Us", “I Knew You Were Trouble” and “Would’ve, Could’ve, Should’ve” are rumored to be about him, whom she dated briefly after collaborating with him on a song, “Half of My Heart”. Their relationship was one of the many mentioned in the song "coney island" from evermore, specifically the line "did I paint your bluest skies the darkest grey" which calls back to a lyric from the song, "Dear John".

Adam Young (not an ex)

The song “Enchanted” is about Adam Young of Owl City. The two never dated, although he did state his interest in her.[5]

Jake Gyllenhaal

Jake Gyllenhaal reportedly spent $160,000 to have her flown over on a private jet for a date.[6] He later broke up with her through text. "We Are Never Ever Getting Back Together", "I Almost Do", "State of Grace", "All Too Well" and its 10 minute version, "Red" and "The Moment I Knew" are rumored to be about him. Additionally, the previously unreleased songs, "Better Man", "Babe", and "I Bet You Think About Me" which were included on the re-recorded version of Red are rumored to be about him. Their relationship was one of the many mentioned in the song "coney island" from evermore, specifically the line, "Were you standing in the hallway with a big cake, happy birthday" which references how Jake didn't show up for Taylor's 21st birthday party which was mentioned in the songs, "The Moment I Knew", and the original 10 minute version of "All Too Well".

Conor Kennedy

He is rumored to be the inspiration behind the song “Begin Again”. Additionally, "Starlight" was written about his grandparents, Robert and Ethel Kennedy.

Harry Styles

"Out of the Woods", "I Know Places", "Clean", "Style", "Is It Over Now?" and "Question...?" are supposedly about Harry. In turn, the One Direction song "Perfect" is rumored to be inspired by Styles' romance with Swift. It's also rumored that the song "Wonderland" may be about him. Their relationship was one of the many mentioned in the song "coney island" from evermore, specifically the line, "and when I got into the accident the sight that flashed before me was your face." Which calls back to their infamous snowmobile accident that was mentioned in the song, "Out of the Woods". The two are still friendly to each other.

Calvin Harris

Taylor and Calvin broke up after 2 years of dating. "Getaway Car", "I Don't Wanna Live Forever", "Bejeweled", and "High Infidelity" are rumored to be about him. Their relationship was one of the many mentioned in the song "coney island" from evermore, specifically the line "But when I walked up to the podium I think that I forgot to say your name" which calls back to when Harris gave an acceptance speech after winning a VMA for co-writing This Is What You Came For at the 2016 MTV VMAs, and didn't thank Swift, who was also a co-writer under the pseudonym Nils Sjöberg. [7]

Tom Hiddleston

Tom Hiddleston and Swift were together from June to September of 2016. "Getaway Car" is rumored to be written about Tom. The pair started dating shortly after her breakup with Calvin Harris.

Joe Alwyn

"...Ready For It?" "End Game" "Delicate" "King of My Heart" "Dress" "Call It What You Want" "New Year's Day" "Lover" "Cruel Summer" "I Think He Knows" "Paper Rings", "Cornelia Street", "London Boy" and more are all supposedly songs about Joe. Their breakup was confirmed by Tree Paine, Swift's publicist a few days after the news was announced.

Matty Healy (not an ex)

Matty Healy and Swift were reportedly seeing each other [8] from May to June of 2023. The pair reportedly had a fling shortly after her breakup with Alwyn, which was confirmed to not be a serious or real relationship. [9]

Table of exes

Name Dated Notes
Joe Jonas July 2008 - October 2008 Broke up over the phone for 25 secs. Inspired “Forever & Always” & "Last Kiss".
Taylor Lautner August 2009 - November 2009 Met on the set of Valentine's Day in a dressing room during filming. Later inspired the song "Back to December".
John Mayer November 2009 - February 2010 The reason of their breakup was never confirmed, as Dear John was released only a few months after them shown being happy, with some thinking it was because of his ego. He inspired the implicit song "Dear John".
Jake Gyllenhaal October 2010 - December 2010 They broke up due to Jake not "feeling it" anymore and the intense media scrutiny that he received while they dated. There were signs of the relationship ending before they officially broke up, like when he didn't show up to Taylor's 21st birthday party, which Taylor wrote about in "The Moment I Knew"[10] and "All Too Well (10 Minute Version)" It inspired many other songs on Red, with the most recognized being "All Too Well" due to the heavily emotional lyrics.[11]
Conor Kennedy July 2012 - October 2012 Broke up due to long-distance issues after his mother's death.[12]
Harry Styles December 2012 - January 2013 Broke up due to a heated argument when they were taking a vacation at the Caribbean, which prompted Taylor to leave the island early in favor to go to U.S[13]
Calvin Harris March 2015 - June 2016 They broke up due to numerous factors, but most of it comes down to the song "This Is What You Came For", which Swift wrote under the pseudonym Nils Sjöberg. She used a pseudonym because she didn't want her relationship to overshadow the song. However, Harris wanted her role minimized to keep it as much as a secret as possible.[14] He later ranted about it on Twitter, which changed public opinion but it also changed his.[15]
Tom Hiddleston June 2016 - September 2016 Their breakup was commonly thought to be due to the pressure of the limelight, with intense media scrutiny. After their relationship, she wrote the song "Getaway Car" which alludes to her feeling horrible about getting in the relationship with him so quickly, and wanting to escape the relationship.
Joe Alwyn September 2016 - March 2023 After almost seven years together, their relationship ended abruptly but amicably. This is Swift's longest relationship to date, she also dedicated many songs to him including "Lover" and "Cornelia Street". Taylor was the one who decided to end the relationship a few weeks within the start of The Eras Tour, because she believed that Alwyn was not fighting for the relationship, as she sings about in "You're Losing Me".

*Some of the notes are not confirmed, and are fan theories based off of songs, with no acknowledgment from Taylor herself or the ex in question.

References

  1. http://www.mtv.com/news/articles/1628878/20091229/swift__taylor.jhtm
  2. http://www.hollywoodlife.com/2010/11/22/taylor-swift-sings-its-too-late-to-apologize-ama-taylor-lautner-back-to-december-twilight/
  3. http://www.youtube.com/watch?v=WsuT3eLGlYw&feature=fvst
  4. http://www.time.com/time/specials/packages/article/0,28804,2035319_2033824_2033807,00.html
  5. http://www.usmagazine.com/entertainment/news/owl-citys-adam-young-2011156
  6. http://www.marieclaire.co.uk/news/celebrity/507226/jake-gyllenhaal-s-160-000-date-with-taylor-swift.html
  7. https://www.usmagazine.com/entertainment/news/calvin-harris-didnt-thank-taylor-swift-at-mtv-vmas-2016-w436652/
  8. https://www.yahoo.com/entertainment/taylor-swift-matty-healy-kiss-205239707.html#:~:text=%E2%80%9CMatt%20is%20attending%20several%20of,been%20linked%20since%20early%20May.
  9. https://pagesix.com/2023/06/05/taylor-swift-was-letting-off-steam-with-matty-healy-after-stifling-joe-alwyn-romance/
  10. https://www.republicworld.com/entertainment-news/music/why-did-taylor-swift-and-jake-gyllenhaal-call-off-their-relationship.html
  11. https://www.capitalfm.com/news/taylor-swift-songs-jake-gyllenhaal-red/
  12. https://www.usmagazine.com/entertainment/news/taylor-swifts-ex-conor-kennedy-nervous-when-she-bought-hyannis-house/
  13. https://www.caribbeanworld-magazine.com/home/magazine/so-what-really-happened-between-harry-styles-and-taylor-swift/#:~:text=But%20now%20the%20truth%20can%20be%20told%20that,plane%20back%20to%20the%20U.S.%20earlier%20than%20scheduled
  14. The Reason Why Taylor Swift and Calvin Harris Broke up (insider.com)
  15. Calvin Harris & Taylor Swift's Breakup: Why He Snapped on Twitter | Billboard | Billboard
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