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A Definitive Ranking Of The 21 Best Taylor Swift Breakup Songs

Tara Bitran |
November 9, 2014 | 7:11 p.m. PST

Staff Reporter

Miss Independent herself on tour for her fourth studio album "Red" in 2013 (@TSwiftOnTour/Twitter)
Miss Independent herself on tour for her fourth studio album "Red" in 2013 (@TSwiftOnTour/Twitter)
We've all been there. The crying, the heartache, the overindulgence of chocolate. The one constant through all of our relationship dissolutions has been none other than Taylor Swift. 

Say what you will about her switch to pop or her drop-off from Spotify; we all can look back on our high school years and remember Taylor Swift's knack for capturing our exact feelings and experiences through song.

SEE ALSO: '1989' By Taylor Swift: Album Review

Fresh off her "1989" album release, here's a throwback to the good old T-Swift songs that got us through our toughest of breakups. 

"Picture To Burn"

As her original breakup anthem off her first album, "Picture To Burn" kicks off Taylor's sassy take-no-prisoners attitude toward guys who've done her wrong. Calling out an ex who takes more pride in his "stupid, old pick-up truck'" than in his relationship with her, Taylor chews him up and spits him out with this song.

"Should've Said No"

Cheating is NOT ok. Period. Looking back on the guy who "should've said no," Taylor expresses her own heartbreak in this rock-infused song inspired by her teen years.

"You're Not Sorry"

Ever had a guy who's mistreated you but was never willing to just apologize? Taylor Swift evokes that exact frustration with "You're Not Sorry." Two words. That's all it takes, man. 

"Tell Me Why"

Tired of a guy consistently trying to put her down, Taylor asks why he consciously chooses to bring her pain rather than support her.


Goodbye to all the guys who have nothing more to say than insults. Newsflash: being mean does not equate to happiness in life.

"I Knew You Were Trouble"

A song that may or may not be about a certain member of One Direction, "I Knew You Were Trouble" is a cause for reflection on all the guys you knew were a bad idea but went after anyway.

"Better Than Revenge"

Clearly not fond of the girl her ex left her for, Taylor warns "the other woman" and her former flame that there's nothing she does "better than revenge."

"The Story of Us"

Every relationship starts out with hope and promise, but in "The Story of Us," Taylor recalls the aching awkwardness between two people once their spark has gone south.


Detailing the whirlwind of colors from the red of "loving him," to the blue of "losing him," and finally to the dark grey of "missing him all alone," Taylor catalogs the full range of emotions one goes through from the beginning to the end of a relationship. 

"Dear John"

A bold yet controversial name for a song, "Dear John" serves as a letter to a fellow famous singer in which Taylor calls him out for taking advantage of her at a young age. The titular John subsequently wrote a song in response, but it's clear Taylor was not happy with how their relationship played out.


"The Way I Loved You"

Taylor notes the acute difficulty of the push and pull between trying to move forward after a previous toxic relationship yet still yearning for that former love in "The Way I Loved You."

"I Almost Do"

 Moving on from the raging hurt, "I Almost Do" recalls the feeling of wanting to call a guy you still have feelings for but stopping yourself just before you do.

"All Too Well"

"All Too Well" was one of the most emotionally taxing songs for Taylor Swift to write for "Red," as the lyrics touch on the precise sadness and turmoil of trying to scythe through one's feelings after a breakup.



Taylor captures the sense of being at a total loss after the bond of a close relationship is broken in "Breathe," as the confusion of trying to determine how to proceed can surely feel like you've got the wind kicked out of you.

"Last Kiss"

In "Last Kiss," Taylor emulates the longing of wanting to return to a former relationship and not knowing where it went wrong.

"Back To December"

Presumably written about a former "Twilight" star, "Back To December" harps upon the regret and guilt of having ended a relationship with a good guy too soon.

"Teardrops On My Guitar"

Oh, Drew. The boy who never saw Taylor as more than a friend until it was too late (he supposedly apologized and asked her out after the song was released only to be turned down). "Teardrops On My Guitar" is an anthem for every girl pining after a guy that "doesn't know she exists."

"Forever And Always (Piano Version)"

Yes; there is a faster version of the song, but the piano version is much softer and painstaking, evoking the hurt and disbelief when trying to discern why a relationship ended. 

"We Are Never Ever Getting Back Together"

One of the catchiest songs off of "Red," "We Are Never Ever Getting Back Together" points out the absurdity and vexation of repeatedly going back and forth from being in a relationship with a guy to breaking up with him. But clearly by the end of the video Taylor and her love interest are never getting back together again, "like, ever."

"White Horse"

Represent for independent women not waiting for a knight on his "white horse" to come around. No guy is perfect, but Taylor's lyrics help to point out that accepting a guy who seems to be an ideal boyfriend but is really unfaithful is certainly not the way to go. Sayonara!

"Begin Again"

Washing away all the pain and hurt, "Begin Again" serves as a willingness to try a relationship with someone new and as an end to the breakup cycle. Props to her for being brave enough to try again.

Personal PSA: Thank you, TSwift, for your relatable lyrics that helped me get through high school.

Reach Staff Reporter Tara Bitran here.



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