All The Songs Taylor Swift Has Sung About Her Ex-Boyfriends

Taylor Swift is incredibly talented and she’s one of the most prolific songwriters in the music industry (all this and she’s not even 30 yet, jeez). But one of the most interesting things about Swift’s songs is that she makes them deeply personal, taking inspiration from her life, and most notably her relationships.

Swift is known to sing about her heartbreak and often delivers scathing songs about her ex-boyfriends. Some of her most famous exes who have served as the inspiration behind her songs include John Mayer, Joe Jonas, Jake Gyllenhaal, Harry Styles and Calvin Harris, to name a few, but below is a more comprehensive list of all the times that Swift sang about her ex-boyfriends — and most of the world sang along with her!

“Ready For It?”

“Ready For It?” is one of Taylor Swift’s newer songs and comes from her 2017 album, Reputation. As for which ex got burned in this track? According to reports, it’s about one of her more recent ex-boyfriends, Calvin Harris who she dated from early 2015 to mid-2016 for a grand total of 15 months.

The lyrics include, “Knew he was a killer first time that I saw him/ Wonder how many girls he had loved and left haunted,” and while that could really be about any of her exes, the clue that everyone has picked up on is the lightning in the music video. This is believed to be a reference to Harris, who used lightning bolts on his record with Rihanna, “This Is What You Came For,” — the very same track that Swift contributed to under a pseudonym.

“Last Kiss”

“Last Kiss” is believed to be penned about Swift’s ex-boyfriend, Joe Jonas. For those who don’t remember, Swift and Jonas briefly dated in 2008, before he dumped her for Disney star Camilla Belle. According to Us Weekly, at the time Swift revealed, “They’ve been together since we broke up. That’s why we broke up — because he met her.”

The main clue as to why “Last Kiss” is about Jonas is apparently in the lyric, “I ran off that plane that July ninth,” which Spin notes is the same day that the Jonas Brothers played a show in 2008.

“Forever and Always”

Swift doesn’t just have one song about her time with Jonas, because “Forever and Always” from her 2008 album, Fearless, is also about him. According to CBS, Swift said that the song was about a relationship where she was with someone who ended up breaking up with her for another girl. And, as we previously established, Jonas reportedly left Swift to be with Camilla Belle.

“Back To December”

The song “Back To December” is reportedly Swift’s one and only apology track for an ex — which makes it a nice change from her usual diss tracks — and it’s for Taylor Lautner. Lyrics include, “You gave me your love/ and all I gave you was goodbye.” But what really points the finger at the male Taylor is “I miss your tan skin, your sweet smile, so good to me, so right / And how you held me in your arms that September night / The first time you ever saw me cry.” She’s seemingly talking about the 2009 VMAs with the infamous Kanye West and she was allegedly dating Lautner at the time. (Also Taylor Lautner is Swift’s only tan ex, pretty much.)

“We Are Never Getting Back Together”

This is perhaps one of Taylor Swift’s most brutal diss tracks, and “We Are Never Getting Back Together” is reportedly about Jake Gyllenhaal — who Swift dated in 2010. In the song, she pokes fun at her ex saying, “You would hide away and find your peace of mind/With some indie record that’s much cooler than mine.” Even though it was penned for Jake, when she performed the song at the 2013 Grammys, we couldn’t help but notice she switched the imitation of the guy in the song to have a British accent… perhaps as a shout out to Harry Styles, with whom she’d recently split at the time.

“Dear John”

There’s no need to look for clues when it comes to who this track is about because it says it right there in the title. “Dear John” was about John Mayer. And not that anyone needed any more confirmation about who the track was aimed at, but Mayer even reacted to it.

In an interview with Rolling Stone in 2012 he said that it really “humiliated him.” The added, “It made me feel terrible. Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.” I mean, it is a BRUTAL diss track.

“Look What You Made Me Do”

The track, “Look What You Made Me Do” is largely believed to be about Calvin Harris. Harris and Swift had a very ugly, and rather public breakup in July of 2016, and it seems that she wanted to have the last word.

The reason everyone is convinced that this song is about Harris is that in the music video she climbs out of a graveyard with the headstone reading “Nils Sjoberg,” the same name she used for her contribution on Harris’s single, “This Is What You Came For” which led to a bit of public bickering when that info went public. There are also some pretty obvious call-outs to Kanye West and Kim Kardashian in this song, but they obviously aren’t her exes…


Like “Dear John,” the title of “Style” pretty much sums up who the song is about, and it’s reportedly about none other than Harry Styles. Clues about the inspiration behind this song are revealed not only by the name of the track, but also about the clothing which is very similar to what Styles is usually seen it. A standout line is: “You’ve got that long hair slick back/ white t-shirt.”

Plus the hottie in her music video looks a heck of a lot like Styles.


The track “Fifteen” was released in 2008 as part of Swift’s Fearless album, and appears to be about her ex-boyfriend, Brandon Borello, who she dated in high school. It’s one of the songs that perfectly and relatably sums up feelings about your first relationship and puppy love — so it makes sense that it was about a non-famous ex-boyfriend.

It was also the world’s introduction to Taylor’s BFF, Abigail, who at this point we all know and love.

“I Knew You Were Trouble”

Styles clearly left an impression on Swift, and it doesn’t appear to have been a good one. She penned the 2012 track “I Knew You Were Trouble” about the One Direction guy, and even admitted to it.

During an interview with Sunday Times, she revealed that her 2012 Brit Awards show performance was so passionate because “it’s not hard to access that emotion when the person the song is directed at is standing by the side of the stage watching.” Styles is British, and at the time he was still apart of the hugely successful boy band, so of course, he was in the crowd. We see you, girl.

“Picture to Burn”

“Picture to Burn” is one of Swift’s first songs about a former lover (it was released in 2006) and is thought to be about her ex-boyfriend, Jordan Alford — another unfamous guy she dated in high school. Alford is now married, and his wife, Chelsea, who was also one of their classmates, has previously spoken about the diss track.

Chelsea said in an interview, “They dated in freshman year. ‘Picture To Burn’ is about him. Because he’s always had big old trucks and stuff.” Lyrics in the song include “I hate that, Stupid old pickup truck,” so yeah — we’ll take that explanation.


The track “Enchanted” is reportedly about Owl City singer, Adam Young. Although Young was never technically Swift’s ~boyfriend~, the pair did have a flirtation. Swift addressed the track during an interview with Yahoo! Music and claimed that it was “about this guy that I met in New York City, and I had talked to him on email or something before, but I had never met him. And meeting him, it was this overwhelming feeling of, I really hope that you’re not in love with somebody.”

Young also commented on his “relationship” with Swift and revealed he was shocked (but undoubtedly flattered) that she penned a song about him.

“State of Grace”

“State of Grace” is reportedly about bad boy Jake Gyllenhaal yet again, who appeared to leave Swift with a massively broken heart. Some of the clues found in this track include the lyrics, “Just twin fire signs/ four blue eyes,” and both Gyllenhaal and Swift have blue eyes and are the same star sign (Sagittarius). Clever.

“Should Have Said No”

Swift wasn’t always dating celebrities, and one of her first boyfriends, Sam Armstrong, also has a track about him. The track “Should Have Said No” comes from her 2006 debut album and is believed to be about Armstrong, who reportedly cheated on Swift when they were in high school. Classy guy! (Sure he’s regretting it now.)

“The Story Of Us”

Mayer inspired quite a few songs it seems — Swift likes to publicly share her relationships and fans have come to expect it — and the second on this list is “The Story Of Us.” While “Dear John” was a lot more obvious, this song reportedly details how Swift felt after their breakup.

Speaking to USA Today after the song’s release, Swift said,”‘The Story of Us’ is about running into someone I had been in a relationship with at an awards show, and we were seated a few seats away from each other. I just wanted to say to him, ‘Is this killing you? Because it’s killing me.’ But I didn’t. Because I couldn’t. Because we both had these silent shields up.” Fans may remember, both Swift and Mayer performed at the 2010 CMT Awards.

“Begin Again”

Swift dated Connor Kennedy in the summer of 2012, and while the relationship was very brief, it is believed to be the inspiration behind “Begin Again.” He was reportedly also Swift’s first boyfriend following her messy breakup with Gyllenhaal, and the timeline seems to fit. The song’s pretty complimentary about the Kennedy while throwing pretty significant digs at her movie star ex. Lyrics include, “I think it’s strange that you think I’m funny ’cause he never did / I’ve been spending the last eight months / Thinking all love ever does is break and burn and end / But on a Wednesday in a cafe I watched it begin again.”

“Call it What You Want”

This entry is a little different to the others on the list, because “Call it What You Want” is reportedly about actor Joe Alwyn, who Swift is currently dating. The relationship was first reported in May of 2017, and at the time the pair were said to have been dating for several months. They have kept their relationship out of the public eye — a very different approach to how Swift handled her last relationship with Tom Hiddleston.

This Taylor Swift song is apparently about Alwyn because of the lyrics, “My baby’s fly like a jet stream high above the whole scene / Loves me like I’m brand new.” It also references this muse’s reaction to the fallout with Kimye, signifying a more recent relationship.

“Out of the Woods”

Some people think that “Out of the Woods” is about Harry Styles, as well. Several publications have noted reasons why this song could be about the singer, with Billboard pointing out that the song includes the lyrics, “We were built to fall apart / Then fall back together” which fits with the couple’s rocky on-and-off again relationship. And the most obvious part of the song is “Your necklace hanging round my neck / The night we couldn’t quite forget / When we decided / To move the furniture so we could dance / Two paper airplanes flying, flying.” The former couple wore matching paper plane necklaces when they were together so that seems as close to evidence as we could get.

“All too Well”

“All Too Well,” which was released in 2012, is apparently another song about Gyllenhaal. The story is set in autumn and is about a couple taking a trip together. According to a report by People magazine in November of 2010, the then-couple were seen getting maple lattes together at a coffee shop not far from where Gyllenhaal’s sister, Maggie Gyllenhaal lives.

Then there is this clue in the lyrics: “Left my scarf there at your sister’s house/ And you still got it in your drawer even now.” … YEP, sounds about right!

Share 0
Tweet 0
Pin it 0
Leave a Reply

Your email address will not be published.

Related Posts