Top 10 Taylor Swift Break Up Songs

Her first of nine Top 20 hits, 'Teardrops on My Guitar' is about Taylor's real-life classmate crush, Drew, and how he had feelings for someone else. Although fittingly written in the perspective of a 16-year-old, the song still tackles the feeling of unrequited love, something we’ve all experienced in high school: “He says he’s so in love / He’s finally got it right / I wonder if he knows / He’s all I think about at night.”

Swift relives the pain and heartache of a break up in this melancholy, painful track from ‘Speak Now.’ “Come on, come on don’t leave me like this / I thought I had you figured out / Something’s gone terribly wrong, your all I wanted,” Taylor pleads, wanting another chance to make things right.

This particular story was inspired after Swift had a run-in with an ex at the 2010 CMT Music Awards. "Now I'm standing alone / In a crowded room / And we're not speaking / And I'm dying to know / Is it killing you / Like it's killing me?" Taylor sings over heavy percussion and electric guitar. Ugh, no wonder she was "nervously pulling at [her] clothes." We would be too.

While Taylor Swift chooses to neither affirm nor deny that this song or “letter” is about John Mayer, we do know she had a short fling with the guitar aficionado while lending her vocals for his 2010 track ‘Half of My Heart.’ Swift sings: “You paint me a blue sky and go back / And turn it to rain / And I lived in your chess game / But you changed the rules every day / Wonderin’ which version of you / I might get on the phone, tonight.”

Another break up song Taylor wrote in high school, ‘Tim McGraw’ is about her then-boyfriend who was about to move away to college. While reminiscing about their relationship, Taylor thinks of their favorite Tim McGraw song — to be identified later as ‘Can’t Tell Me Nothin’.'

‘Back to December’ finds Swift apologizing to a boy she may have not appreciated back in December of 2009. “This is about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him,” Swift tells E! Entertainment. “So, this is a song full of words that I would say to him that he deserves to hear.” Like ‘Dear John,’ Taylor stays mum, but we all know she dated Taylor Lautner towards the end of ’09.

The slow-tempo break up song ballad has us reminiscing on the good times of being in love — the dancing, his step, handshake, and his kiss. “So I’ll watch you live in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe / And I keep up with our old friends just to ask them how you are.”

When Taylor’s pissed off, you'll know it, evident in this break up song laced with country attitude. Off Swift’s self-titled, debut album, the song easily writes off an old flame, as shown in the Trey Fanjoy-directed video. “The storyline of the video is," Taylor slyly states, "if you break up with me, my band will ransack your house.” Boys, you were warned!

A banjo rock-infused track, ‘Should’ve Said No,’ stems from the words her ex pleaded to her after Taylor found out he cheated. Although not as angry as ‘Picture to Burn,’ the song dabbles on the morals and lessons Swift learned from her 16-year-old relationship.

A fairytale without the happy ending, ‘White Horse’ portrays an unfaithful boyfriend who Taylor sees originally as the perfect guy in ‘Love Story.’ Co-penned by Swift and Liz Rose, the piano ballad, from 2008′s ‘Fearless’ album, went on to win two Grammy Awards for Best Country Song and Best Female Country Vocal Performance.