A Deep Dive Into Taylor Swift’s Ex-Boyfriends & All The Spicy Songs She Wrote About Them

Taylor Swift‘s freshest album The Tortured Poets Department is here! So in celebration of all the rumours about how ~spicy~ this project is going to be, we’ve pulled a Tracy Grimshaw and investigated all of Swift’s lyrics while attaching them to her former flames.

In the lead-up to the release of The Tortured Poets Department, there were clues, theories and leaks. Ever since all of these little trickles of Swift content surfaced on social media, folks have been compiling threads of what the new album was going to be about — but most importantly, who.

I mean, most people who grew up watching Swift’s rise to stardom would’ve noticed that the star likes to communicate through her craft. And let’s be real, she does the most tea spilling about her exes through these songs.

So far, the front-running inspo for The Tortured Poets Department is Joe Alwyn, Swift’s most recent ex. But surprisingly, Matty Healy has been tipped as the album’s subject matter due to some of the naughty leaks. Tsk tsk.

As we wait for the big drop, we’ve decided to do some digging and see what tea has been spilled by Mother Swift alongside a timeline of her relationships!

So without further ado…

Here’s a timeline of Taylor Swift’s relationships and the key songs that spill some major tea

1. Taylor Swift and Joe Jonas (2008)

This was my Avengers: Infinity War!!! (Image source: Getty Images / Jeff Kravitz/FilmMagic)

Joe Jonas and Taylor Swift dated briefly during his peak Disney era — something Swift should’ve added in her Eras Tour. The pair only dated for a couple of months before they reportedly had a bitter break-up.

According to Swift, during her 2009 Saturday Night Live monologue, she took aim at her former Camp Rock flame.

“You might think I’d bring up Joe, that guy who broke up with me on the phone, but I’m not gonna mention him in my monologue,” Swift sang.

“Hey Joe, I’m doing real well!”

(Image source: YouTube / Saturday Night Live)

Beyond that, Swifties believe that their fave popstar has a variety of songs inspired by the Camp Rock actor.

According to one Redditor on the r/TaylorSwift subreddit, the song included “Forever & Always”, “Last Kiss” and “Holy Ground”.

During an interview on The Ellen Show (hosted by *that* Ellen Degeneres) Swift confirmed that “Forever & Always” was about Jonas.

(Image source: YouTube / The Ellen Show)

Some of the lyrics of “Last Kiss” have been tipped to be about the demise of her relationship with Jonas.

The lyric in question reads: “I never thought we’d have a last kiss. I never imagined we’d end like this. Your name, forever the name on my lips.”

And “The Holy Ground” mentions a “first-glance feeling on New York time”. Some Swifties believe that this relates to when Swift performed with the Jonas Brothers at Madison Square Gardens.

Following those songs, the Redditor also said that “Mr Perfectly Fine” and “Better Than Revenge” was also about Jonas.

byu/honeybearhufflepuff from discussion

2. Taylor Swift and Lucas Till (2009)


Y’all may know him as the bloke from the “You Belong With Me” video but real OG’s know him from the Hannah Montanna Movie.

Although most of T-Swizzle’s flames get a special track, he did not. Soz mate!

3. Taylor Swift and Taylor Lautner (2009)

Original mewing king. (Image source: Getty Images / Jean Baptiste Lacroix/WireImage)

Taylor Lautner AKA The BEST Taylor Swift Ex has had a song written about him.

Alongside Joe Jonas, Lautner was mentioned in the monologue but in a positive way as it seemed that the pair were dating at the time.

It is reported that Lautner inspired the song “Back To December” as the lyrics read “your tanned skin, your sweet smile.”

Do you know who has tanned skin and a sweet smile?

This Alpha wolf, baby!

(Image source: Twilight)

Swifties have also speculated that “Midnight Rain” is about Lautner. However, they’ve since argued that it’s about Tom Hiddleston — which we will get to in due time.

4. Taylor Swift and John Mayer (2009)

(Image source: by Dimitrios Kambouris/Getty Images for VEVO)

Kicking off with the most obvious track: “Dear John”.

In the lyrics, Swift took aim at a variety of factors in their relationship and spilled some piping HOT TEA about their breakup.

One of the most notable lines, “Don’t you think I was too young to be messed with?”, was ‘yuge a reference to John Mayer‘s 12-year age gap with Swift.

One Swiftie on Reddit also pointed out that the song’s guitar riffs mimicked Mayer’s music style.

byu/AJillianThings from discussion

After the song’s release, Mayer told Rolling Stone that the song made him “feel terrible because [he] didn’t deserve it”. LMAO anyways, he also added: “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.”


5. Taylor Swift and Cory Monteith (2010)

<3. (Image source: Getty Images / Rick Diamond/WireImage)

Taylor Swift’s relationship with Cory Monteith was never confirmed. However, some Swifties believe that the song “Mine” could be about the Glee star.

But Redditors have since debunked it, believing that it could be about a different Cory.

6. Taylor Swift and Jake Gyllenhaal (2010 – 2011)

The main T-Swizzle song that Swifties link back to Jake Gyllenhaal is “All Too Well”.

You see, there has been a running theory that Gyllenhaal bloody nicked Swift’s scarf and has been wearing it around the town, at the time of their breakup and beyond.

In “All Too Well” Swift sings, “Left my scarf there at your sister’s house and you’ve still got it in your drawer even now.”

When the track dropped, Swities hassled Gyllenhaal’s sissy Maggie Gyllenhaal so much she responded on Watch What Happens Live with Andy Cohen.

“You know, I never understood why everybody asked me about this scarf. What is this?“ she said.

7. Taylor Swift and Adam Young (2011)

This has never been confirmed to be a real relationship. However, it’s been speculated that “Enchanted” was about the Owl City singer.

Adam Young then covered the song and left Swift a note!!!

Again, it’s never been confirmed from Swift’s camp but Young’s version of the song is so cute.

8. Taylor Swift and Zac Efron (2012)

(Image source: Christopher Polk/Getty Images for PCA)

The rumours of this relationship came off the back of The Lorax. You see, ZacEfron and Taylor Swift voiced each other’s love interests for the movie. Naturally, folks thought they had some off-screen romance brewing.

The pair have never confirmed their relationship, and even denied their relationship via a musical skit on The Ellen Degeneres Show.

(Image source; YouTube / The Ellen Show)

9. Taylor Swift and Conor Kennedy (2012)

Taylor Swift’s relationship with Conor Kennedy was quite controversial due to their age gap and rumour that Swift had crashed his cousin’s wedding, LMAO.

Song-wise, it is believed that Swift’s track “Everything Has Changed” was about Kennedy. Per Vulture, a secret message in the lyrics — where some letters that are capitalised spell out “HYIANNIS PORT”.

Although the spelling is incorrect, some people believed this to be a nod to Hyannis Port, Massachusetts. It was reported that Swift had bought a property there to live near her Kennedy beau.

“Begin Again” was reportedly about Kennedy as well.

10. Taylor Swift and Harry Styles (2012 – 2013)

(Image source: Getty Images / David Krieger/Bauer-Griffin/GC Images)

Starting off with the most obvious one: “Style”. Duh, the last name!

It is also speculated that “I Knew You Were Trouble” was also about the One Direction member as well as “Out Of The Woods”.

The reason as to why punters believe that “Out Of The Woods” was about Styles, was due to some of the lyrics.

“Your necklace hanging from my neck. Remember when you hit the breaks too soon? Twenty stitches in the hospital room. When you started crying, baby, I did too,” Swift sang.

Some people speculate that the “breaks” part is a reflection of their breakup as well as a snowmobile accident that involved Styles.

Redditors on the r/TaylorSwift subreddit also have speculated that “Slut! (Taylor’s Version) (From The Vault)” is about her fling with the “Watermelon Sugar” singer due to the lyrics, “Everyone wants him. That was my crime”.

Let’s not forget how vicious Directioners were to Swift when their relationship first surfaced. It was bloody BRUTAL.

Slut! (Taylor’s Version) (From the Vault) is referring to the Harry Styles stans, right?
byu/Darling_Ragdoll inTaylorSwift

11. Taylor Swift and Calvin Harris (2015 – 2016)

(Image source: Getty Images / Jeff Kravitz/BMA2015/FilmMagic)

Calvin Harris and Taylor Swift dated for a couple months!!! As someone who has been chronically online since the 2010s, their beach photos have been engrained into my mind.

Following their split, some Swifties have speculated that “Bejeweled” is about Harris, however, it’s been argued that the song is actually about Joe Alwyn — which makes more sense, IMO.

Swifties in the r/TaylorSwift subreddit have also shared that “Getaway Car”, “Dancing With Our Hands Tied” and “So It Goes” are about her relationship with the producer.

Ok but which songs are about Calvin Harris?
by inTaylorSwift

12. Taylor Swift and Tom Hiddleston (2016)

(Image source: Getty Images / starzfly/Bauer-Griffin/GC Images)

Some people have linked “Getaway Car” to Tom Hiddleston with one Swiftie saying that he’s the one “driving the getaway car in getaway car”.


The main lyric that convinced fans that it was about the Loki actor reads: “I wanted to leave him, I needed a reason.”

13. Taylor Swift and Joe Alwyn (2017 – 2023)

(Image source: Getty Images Jackson Lee/GC Images)

Oh me, oh my. This one is definitely a more JUICY situation — especially if you love goss. I feel like if I were to explain all the songs about Joe, we’d probably need a whole new website, BUT I’ll give ya quickie summary of the songs that are rumoured to be about the British Actor.

Joe Alwyn is believed to have inspired a buttload of songs. Thankfully, this Swiftie Redditor has shared the rumoured songs in chronological order.

u/Badgerell you icon!

byu/zelenadragon from discussion

Although it’s not on this Redditor’s list, it has been speculated that “Bejewled” is about the actor and how Swift felt trapped in the relationship.

“Don’t put me in the basement when I want the penthouse of your heart,” the lyrics read.

“You’re Losing Me” was also a big one that people immediately linked to Alwyn as it kinda gave an insight into how Swift felt towards the end of their lengthy relationship.

In the song, Swift contemplates if the relationship is even worth saving and how she gave the person “all my best me’s”.

In the bridge, she took aim at herself, singing: “And I wouldn’t marry me either. A pathological people pleaser.” 

Now that the Tortured Poets Department is coming out, there’s bound to be a bunch of songs about Alwyn surrounding the end of their relationship.

Some folks have linked the songs “So Long, London”, “But Daddy I Love Him”, ” Florida!!!” and “Guilty As Sin?” to the ex.

14. Taylor Swift and Matty Healy (2023)

(Image source: Getty Images / Robert Kamau/GC Images)

Although the pair were seen holding hands and being all couple-like, their relationship was never confirmed.

Following the announcement of The Tortured Poets Department, some Swifties reckon some songs — “Down Bad” and “Fortnight” — could be about the 1975 frontman.

15. Taylor Swift and Travis Kelce (2023 – present)

KARMA IS THE GUY ON THE CHIEFS.(Image source: Getty Images / Patrick Smith)

There are obviously no new songs about Travis Kelce just yet, but she did change the lyrics to “Karma” while on tour to pay homage to her Super Bowl-winning BF.

“Karama is the guy on the Chiefs, coming straight home to me,” she sang.

Not to jinx anything, but I reckon Swift and Kelce could be endgame.

Fingers crossed for 50 more albums just about Swift and her loveable himbo!