Throwback Thursday: Taylor Swift’s Greatest Flings & Songs About Them

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If there’s one woman whose love life always has the media’s attention and is constantly making tabloids, it’s Taylor Swift. Taylor Swift has seen a lot of lovers and a lot of drama in her life, and it’s no wonder that a lot of this drama seeps into her musical talent. Her lyrics speak to the lovesick and the lovelorn. The Country Pop darling is known for writing songs about the ‘ghost of boyfriend’s past’ and has the lyrics and her exes… pretty much every time.

Here are some of our favorite Taylor Swift flings and the many songs she ‘allegedly’ wrote about these unsuccessful romances.

Joe Jonas

Dated From: July 2008 -October 2008

Joe Jonas’s infamous dumping of Taylor Swift over a 27-second phone call is something everybody remembers. Last Kiss and Forever and Always were two of the many songs she’s written about her Disney heartthrob ex-boyfriend.  

Lucas Till

Dated from: March 2009 – April 2009

In the song, You Belong With Me, Taylor Swift and co-star Lucas Till showed brilliant on-screen chemistry and won each other’s hearts. However, their relationship was short-lived, and the breakup didn’t involve a lot of drama, which is probably why Taylor doesn’t have a sassy song about him. Lucas said that it didn’t work out between them because he liked Taylor as a friend. 

Taylor Lautner

Dated From: August 2009 – December 2009

Remember when in Back to December Taylor apologies to an ex for a ‘rough night’? Fans think that is a reference to the night she dumped Taylor Lautner. This may just be because of the words’ tan skin’ and ‘sweet smile,’ and Taylor Lautner has both of those things and more. The duo met on Valentine’s Day and caught each other’s eye. 

Jake Gyllenhaal

Dated From: October 2010 – January 2011

Jake Gyllenhaal and Taylor Swift shared something of a whirlwind two-month romance before Jake dumped her, leaving her very upset. 

Her song Mr. Perfectly Fine is heartbreaking, with lyrics that go, “Hello, Mr.’ Perfectly fine’ How’s your heart after breaking mine?” She uses the phrase ‘casually cruel,’ which is also a part of her song All Too Well, which is said to be about Jake.

Harry Styles

Dated From: Late 2012 – Early 2013

Harry Styles and Taylor had a romance that may have been brief but was very controversial. Fans think that the entire album 1989 was based on her fling with the British singer. I Knew You Were Trouble isn’t just about Harry, but the music video actor also bears an unmistakable resemblance to him. 

Calvin Harris

Dated From: February 2015 – June 2016

Ellie Goulding introduced the two, and they immediately clicked. This relationship was one of Taylor’s longest-standing ones. In her song Look What You Made Me Do, she refers to Harris when she crawls out of a graveyard with a headstone that read ‘Nils Sjoberg,’ which was the pseudonym she used on Harris and Rihanna’s famous track This is What You Came For.

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