Taylor Swift’s Songs and the Boyfriends They’re About

By C. Murph | Monday Monday Staff -    2016-09-30

Taylor Swift
Swift and her love life (photo from www.billboard.com)

I write this not as a burn on Taylor or as a way to put her down. I just find it interesting how a songwriter’s real life comes out in their music — and how some artists are much more open about personal stuff in their songs.

Swift stays in the news, for better or worse. Whether it’s her feud with Kanye, her new music, or — what seems to be most often — her love life. (Why the press is so obsessed with this part of her life, I don’t know).

So, Taylor, don’t take this the wrong way, but this article covers the songs you wrote about some of your boyfriends (seemingly).

Everyone else, try to appreciate Taylor’s honesty.

Joe Jonas — July 2008 to October 2008

Taylor SwiftApparently, the couple broke up during a 27-second phone call, and the songs that Taylor wrote from her experiences with Jonas were both harshly honest — with “Last Kiss” and “Forever and Always” — and positive — with “Holy Ground.”

Taylor Lautner — August 2009 to December 2009

Taylor SwiftOn Swift’s single “Back to December, she apologizes to one of her ex-boyfriends, most likely Lautner. She says sorry for a rough night, which could have been when she broke up with the actor, citing his “tan skin” and “sweet smile.”

John Mayer — December 2009 to February 2010

Taylor SwiftEveryone knows about “Dear John.” In that song, Taylor opens up and sings, “Don’t you think I was too young to be messed with? The girl in the dress cried the whole way home. I should’ve known.”

Jake Gyllenhaal — October 2010 to January 2011

Taylor SwiftTaylor told NPR that “The Last Time” is about an “experience I had with someone who was kind of this unreliable guy. You never know when he’s going to leave, you never know when he’s going to come back, but he always does come back.” It’s very likely that when she sang, “Put my name at the top of your list,” she had Jake in mind.

Zac Efron — February 2012 to March 2012

The only Swift song that Zac was involved in was a parody of Foster the People’s “Pumped Up Kicks,” disregarding any rumors that the two were dating.

Conor Kennedy — July 2012 to October 2012

Taylor SwfitDuring an interview with Ryan Seacrest, Taylor said the single “Begin Again” was about “when you’ve gotten through a really bad relationship and you finally dust yourself off.” At that time, she was dating Conor. So when she sang, “I think it’s strange that you think I’m funny ’cause he never did,” was it about him?

Harry Styles — December 2012 to January 2013

Taylor SwiftAfter Taylor and the One Direction member apparently had “a thing,” Taylor came out with “I Knew You Were Trouble” about Styles. Right after the two broke up, she tweeted her lyrics: “…’til you put me down.” “Out of the Woods” from her album “1989” is also widely assumed to be about Harry because it references their December romance and a snowmobile accident.

Boy, that’s as honest as a songwriter can get.

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C. Murph

C. Murph is a freelance writer who lives in Pennsylvania.

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