The most iconic Taylor Swift songs about her exes

From “Picture to Burn” to “All to Well”, these are some of the most iconic Taylor Swift songs about her exes.

Whether you like her or not, it is undeniable that Taylor Swift is an icon and a force to be reckoned with. The woman has caused a surge in NFL viewership just because of her presence and is performing her concert all across the globe that lasts three hours, sometimes in pouring rain. If that isn’t a pop culture icon, I don’t know what is. 

It’s also not a mystery that she’s a fantastic songwriter and can weave stories through her songs. However, it’s Taylor Swift’s songs about her exes and her experiences in her past relationships that fans love. It’s not that they’re revelling in her pain but more that she’s able to articulate the pain of a breakup very well. In fact, she even says in the Eras Tour movie that she loves writing breakup songs. 

Taylor has rarely outright confirmed which song is about which ex but that’s exactly the detective work Swifties love to delve into, and throughout the course of her ten albums, Swifties have determined which song is attributed to which ex. This is not an exhaustive list of songs or exes, but we’ve picked out some of the most well-known ones. Swifties will know this by heart. Non-Swifties can take a listen and appreciate the story behind it. Haters, well, are gonna hate, hate, hate, hate, hate. 

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8 of the most iconic Taylor Swift songs about her exes

“Picture to Burn” from Taylor Swift (2006)

Inspo: Jordan Alford

Iconic Lyric: “You’re a redneck heartbreak who’s really bad at lying”

Jordan Alford is no actor, singer, or any type of celebrity, but he was Taylor’s high school sweetheart. Clearly, it didn’t end well. That’s because he cheated on her with her best friend. Little did he know that he would kick off Taylor’s proclivity for immortalising the deeds of her exes in songs. This is one of her early ones so her country influence is still evident but it was a sign of things to come—and a warning for those who would break her heart that none of her exes seemed to heed. 

“Dear John” from Speak Now (2010)

Inspo: John Mayer

Iconic Lyric: “Well, maybe it’s me and my blind optimism to blame / Or maybe it’s you and your sick need to give love then take it away”

Taylor and John Mayer dated when Taylor was just 19 and he was 31. She does not hold back in taking a swipe at Mayer. “Don’t you think I was too young to be messed with?” goes the chorus. “Don’t you think nineteen’s too young to be played by your dark, twisted games when I loved you so?” Yikes.

To everyone’s surprise, John Mayer actually reacted to the song, telling Rolling Stone, “It made me feel terrible because I didn’t deserve it… It was a really lousy thing for her to do.” Swifties would say otherwise, but Mayer, being a songwriter himself, responded in kind with a song about Taytay entitled “Paper Doll”. “You’re like twenty-two girls in one and none of them know what they’re runnin’ from,” referencing one of her songs and a line from “Dear John”. Double yikes. 

“Style” from 1989 (2014)

Inspo: Harry Styles

Iconic Lyric: “Could end in burning flames or paradise”

This was yet another brief love affair but it was impactful enough for Taytay to write this song. He allegedly is also the inspo for many of the songs in this album so it must have been one heck of an eventful relationship since it only lasted for a month or less. Judging from the lyrics, there doesn’t seem to be any bad blood (heh) between them though. I mean, there’s nothing that scathing compared to her other songs. 

“Forever and Always” from Fearless (2008)

Inspo: Joe Jonas

Iconic Lyric: “Was I out of line? / Did I say something way too honest, made you run and hide / Like a scared little boy”

Since Joe Jonas infamously broke up with her “over the phone in 25 seconds”, at least according to Taylor, then there’s no way that the songs about him will picture him in any kind of positive light. In a rare move, Taylor actually confirmed that this song was about him on Ellen and said that the breakup was “ouch”. Jonas was Taylor’s first celebrity boyfriend and had to navigate the fact that he was everywhere since the Jonas Brothers were also on the rise after their breakup, something she also talked about on Ellen. In fact, it may be one of the only interviews where she talks in length about an ex and a song inspired by them. It makes you realise why Taylor hung out with Sophie Turner after her divorce from Jonas was confirmed. 

“Midnight Rain” from Midnights (2022)

Inspo: Tom Hiddleston

Iconic Lyric: “He wanted a bride, I was making my own name”

Fans have speculated that this song was about Taytay’s three-month romance with the Marvel actor back in 2016. Hiddleston had nothing bad to say during or after their relationship. One can only wonder what the reason for their breakup was, but Taytay seems to be apologetic in her songs allegedly about Hiddleston. Even “Getaway Car”, another song attributed to Hiddleston, goes, “Should’ve known I’d be the first to leave / Think about the place where you first met me.” Fans have speculated that Taytay felt guilty because Hiddleston was a rebound after her breakup with Calvin Harris. Hiddleswift will be fondly remembered though, and Hiddleston wearing an “I <3 T.S.” shirt will remain iconic. 

“Back to December” from Speak Now (2010)

Inspo: Taylor Lautner

Iconic Lyric: “Because the last time you saw me is still burned in the back of your mind / You gave me roses and I left them there to die”

Hiddleston wasn’t the first ex that Taylor wrote an apologetic song to. That honour goes to Taylor Lautner who she met on the set of Valentine’s Day. Again, Taylor Lautner seems to bear no ill will towards, uh, Taylor because he made a special appearance at one of her concerts along with his wife. He and Taytay seem to have ended up as good friends instead, and Taylor Lautner still married someone named Taylor, which was something fans were looking forward to if the actor and pop star ever ended up together. 

“Lover” from Lover (2019)

Inspo: Joe Alwyn

Iconic Lyric: “With every guitar string scar on my hand / I take this magnetic force of a man to be my lover / My heart’s been borrowed and yours has been blue / All’s well that ends well to end up with you”

Joe Alwyn was Taylor’s longest relationship by far and many thought it would go the distance. Alas, we now live in a post-Alswift world, and we await with bated breath just what songs will come out of this breakup. But what’s clear from her songs is that Taytay truly thought this was the one, the relationship that was going to be forever (again, heh). Out of the many songs about Alwyn that she’s written thus far (because there’s definitely going to be more), this one was where Taylor seemed to really bare her heart and soul for Alwyn.

“All Too Well” from Red (2012)

Inspo: Jake Gyllenhaal

Iconic lyric: “And you call me up again just to break me like a promise / So casually cruel in the name of being honest”

The crème de la crème of Taylor’s breakup songs and perhaps every breakup song ever written, the original five-minute-and-a-half runtime of “All Too Well” was already scathing enough. Whatever Taytay and Jake evidently went down in flames (I’m not even trying, these are all just coming out naturally), and it affected her so much that she wrote multiple songs about him. This, of course, is the most iconic because its true unedited cut is ten minutes long, a cut that would later be released in 2021 and would later become known as the definitive version of the song. One can only imagine how Jake must have felt after the song did the rounds once again, and it hasn’t stopped since Swifties all across the globe continue to scream every word of the ten-minute song in her concerts and now even in movie theatres.