A Timeline Of Taylor Swift's Ex-Boyfriends Through Her Breakup Songs | Betches

Taylor Swift

Every Ex-Boyfriend Taylor Swift Has Ever Written A Song About, Proving She's Psycho

By Jane Duh

If there’s one thing we all know about Taylor Swift, it’s that she loves writing songs about the A-listers she’s fucked dated. And that she’s annoying. Okay, that’s two things. Whatever. While we know that each and every one of Taylor’s lyrical roasts are about some real man out in the world, it can be hard for anyone but Taylor’s most dedicated stans to keep together who she’s dated and when, let alone which songs correspond to their breakup. Given that Taylor Swift’s love life is a literal rubix cube of hookups, it can be hard to figure out which of Taylor’s boyfriends each of her songs is about. Like, when was she dating Joe Jonas again? Was that really NINE years ago? Has Taylor Swift really been famous for the entirety of my adult life? How can one person be so annoying yet so good at writing breakup songs?


Well, I can’t offer you an explanation for the last one, but what I can offer you is a detailed timeline of all of Taylor’s exes and the songs she wrote about them, because I have way too much time on my hands, apparently. Use this info to wow your friends at a party, or make them concerned for your mental health. Either way, it’s free attention.

Taylor Swift, 2006

Taylor Swift’s debut album, from back when she was a country star or whatever, is mostly about the high school guys she dated who people only know about now because Taylor became so famous. Still, this album was a pretty good precursor to all the take-downs of her celebrity boyfriends yet to come. In fact, we actually know a surprising amount about the boys in this album, all because they made the mistake of dating Taylor Swift when she was in high school.

"Picture To Burn"
ABOUT: Jordan Alford
WHO HE IS: High school boyfriend
THE EVIDENCE: Friends have said the video “contained references to their relationship.” Because just writing a song about someone is not enough.

"Teardrops On My Guitar" 
ABOUT: Drew Hardwick
WHO HE IS: High school crush
THE EVIDENCE: Well I mean, she literally says his name at the beginning of the song. Bold move for a not-yet-famous 16-year-old with crimped hair. Taylor truly has been insane for years.

Teardrops On My Guitar

"Our Song"
ABOUT: Brandon Borello
WHO HE IS: Longterm High School Boyfriend, he and Taylor dated for like, a very long time apparently.
THE EVIDENCE: Originally performed at HS talent show when the two of them were dating. You know, before she realized she could start getting with Jonas brothers and shit.

"Should've Said No"
ABOUT: Sam Armstrong
WHO IS HE: HS boyfriend who cheated on her. Little did he know that the girl he was cheating on would become a mega famous pop star known for her epic breakup anthems.
THE EVIDENCE: In the liner notes for this song every S A and M that are in order were capitalized because Taylor Swift is nothing if not a shady, shady bitch who lacks subtlety.

"Tim McGraw"
ABOUT: Brandon Borello
WHO HE IS: Again, this was her longterm high school boyfriend who may or may not be the only ex that Taylor Swift actually likes.
THE EVIDENCE: Lyrics about breaking up for college, which they did. I guess the only way to escape Taylor’s rage is to break up mutually, for geographic reasons.

Fearless, 2008

Fearless still falls into Taylor Swift’s pop-country phase, but also represents a definite shift in her dating habits because it was released after her first major celebrity relationship with Joe Jonas. It would be only A-lister for Taylor from here on out.

"Fifteen"
ABOUT: Brandon Borello
WHO HE IS: Her longeterm high school boyfriend, again. Taylor clearly was still hung up on this relationship despite the whole “getting super fucking famous” thing. Maybe the reason Taylor can’t seem to hold down a relationship is because her true love was Brandon the whole time? Just a thought.
THE EVIDENCE: This is who she was dating when she was 15 so yeah the song is about him.

Fifteen Taylor Swift

"Hey Stephen"
ABOUT: Stephen Liles
WHO IS HE: Some musician who toured with Taylor and is part of the country duo Love & Theft. This was clearly Taylor’s first attempt at celebrity dating, but I think we all knew she could do better.
THE EVIDENCE: His name is literally the title of the song.

"Forever & Always"
ABOUT: Joe Jonas
WHO IS HE: Arguably the hottest Jonas brother, Joe was Taylor’s first big celebrity relationship. The two dated from July 2008 to October 2008 at which point Joe dumped Taylor over the phone. Big mistake, Joe. Huge.
THE EVIDENCE: Lyrics about “staring at the phone” after Taylor had gone all over television to tell people Joe had dumped her over the phone. Clearly she wanted people to get the reference. Very subtle, Tay.

Speak Now, 2010

By 2010, Taylor is still fucking with the country vibe, but has fully converted to only dating celebrities. In the two years between 2008 and 2010, Taylor had already gone through one Jonas brother, a Glee castmember, one of the Twilight guys, and an alcoholic John Mayer. Girl clearly had an agenda, and honestly her ability to cross pop culture heartthrobs off her “to do” list is kind of inspiring.

"Mine"
ABOUT: Cory Monteith
WHO HE IS: Late great star of Glee. RIP.
EVIDENCE: Before Cory and Leah Michele were a thing, he had a month long fling with Taylor Swift. And a month is all Taylor needs to write a song. This one is about a boy she barely knew, and many people think she’s referring to Monteith.

"Back To December"
ABOUT: Taylor Lautner
WHO HE IS: The werewolf from Twilight who falls in love with Kristen Stewart’s baby in the end.
EVIDENCE: Okay, so this is a bit of a journey. Basically, Swifties think this song was meant to be an apology from Taylor S to Taylor L after they’d just broken up because when Taylor S performed this song at the AMA’s she added “it’s too late to ‘pologize” at the end, which taken to be a reference to a parody video Taylor L made for “Apologize” by One Republic around that same time. Like I said—a rubix cube of hookups.

"Dear John"
ABOUT: John Mayer
WHO HE IS: Katy Perry’s ex.
EVIDENCE: As we all know, 20-year-old Taylor Swift briefly dated thousand-year-old John Mayer from December 2009 to February 2010, which would eventually spawn the Katy Perry/Taylor Swift rivalry of today (anybody who believes that shit is about a backup dancer is playing themselves). The song both has John’s name in the title and refers to the pair’s age difference, so I think it’s pretty safe to say this one is about John Mayer. Also John Mayer told Rolling Stone the song “humiliated him” which is hilarious considering he had no shame in dating a woman only two years out of high school.

Dear John Taylor Swift

"Better Than Revenge"
ABOUT: Joe Jonas
Evidence: If you thought Joe Jonas was going to get away with leaving Taylor for actress Camilla Belle, then you don’t know Taylor Swift at all. This song goes in not only on Jonas, but his new girlfriend, with lyrics referring to an “actresses” who's "better known for the things that she does on the mattress" (sick burn, Tay!) and the line “she underestimated just who she was stealing from,” which is honestly probably very true.

"Last Kiss" 
ABOUT: Joe Jonas
EVIDENCE: Joe Jonas, you done fucked up now. JJ had to learn the hard way that you do not dump Taylor Swift on the phone for some rando actress without having any less than three pointed breakup songs about you. The timeline of relationship vs. when song was released points to this one being another dig at Joe.

Red, 2012

Red was the first album where we see Taylor make the full shift from country star to pop artist, and honestly, it’s one of her best. Taylor had also had two more years to grow her celebrity fuck list, which is why Red has pound for pound the most songs about the most celebs than any of her previous or later works. Taylor had fully established her reputation as the breakup queen at this point, and Red is basically her just leaning wayyyy into it.

"State of Grace"
ABOUT: Jake Gyllenhaal
Who He Is: Maggie Gyllenhaal’s brother who got to hook up with Heath Ledger in that one movie.
EVIDENCE: Jake Gyllenhaal and Taylor Swift dated from October 2010 to January 2011, which is pretty long in Swift years. As such, basically every song on Red is about Jake Gyllenhaal. The lyric “Twin Fire Signs and Four Blue Eyes” gives this one away. Jake and Taylor both have blue eyes, and they’re both Sagittarius, which is a fire sign.

"Treacherous"
ABOUT: Conor Kennedy
WHO HE IS: A fucking Kennedy.
EVIDENCE: From July 2012 - October 2012, Taylor decided to move away from celbrity A-listers to literal American royalty by dating a Kennedy, and she promptly fucked that relationship right up. The two broke up after reports that Taylor came on wayyyy too strong (the prospect of being the next Jackie O was too much for Taylor to handle). Taylor reportedly straight up followed Conor via private jet to his family vacation on Hyannis Port. T-Swizzle literally bought a house in Hyannis Port, the Kennedys’ favorite vaca spot. The lyric “I’ll follow you home” is supposed to be a (very creepy) reference to this event.

"I Knew You Were Trouble"
ABOUT: Harry Styles
WHO HE IS: Hottest guy in one direction who isn’t Zayn Malik.
EVIDENCE: Taylor gave this one away when she performed the song at the Grammy’s and used the opportunity to show off her mock British accent (needs work, btw). Then, in case Harry didn’t get the message, she went on TV and said of the performance “It’s not hard to access that emotion when the person the song is about is standing off to the side of the stage watching.” Also, Harry Styles is totally trouble, and you would know it if he walked in.

I Knew You Were Trouble

"We Are Never Getting Back Together"
ABOUT: Jake Gyllenhaal
EVIDENCE: One of Red's biggest his is also another one about Jake, and it's fairly obvious. She references his indie band directly here. Also they had like, just broken up. Plus, Taylor stans say that a scarf featured in the music video is identical to one Swift wore on date with Jake. Sidebar: If you’re so into Taylor Swift that you notice something like this, you are disturbed.

"All Too Well"
ABOUT: Jake Gyllenhaal, again
EVIDENCE: It’s this scarf shit again! This song refers to a “scarf” left at “your sister’s house,” which I guess is a reference to a scarf that Taylor left at Maggie Gyllenhaal’s house. Very deep.

"Everything Has Changed"
ABOUT: Conor Kennedy
EVIDENCE: As you may or may not know, Taylor Swift has taken to hiding messages in the liner notes of her CDs. This made more sense when people were actually buying CDs, but whatever. The hidden liner note message for this song reads “HYIANNIS PORT,” which is a misspelled version of “Hyannis Port,” aka the place where 22-yea-old Taylor Swift stalked 18-year-old Conor Kennedy until (we assume) he dumped her out of fear.

Everything Has Changed

"The Last Time"
ABOUT: Jake Gyllenhaal
EVIDENCE: Okay so Taylor Swift must have really, really liked Jake Gyllenhaal. I mean, he’s cute and all but like, is he 4+ songs on what is arguably your best album cute? IDK. Swifties say this song is about Jake because of the lyric “Put my name at the top of your list,” since Jake had been linked to both Rachel Bilson and Anna Kendrick at the time.

"Holy Ground"
ABOUT: Joe Jonas
EVIDENCE: Just when you thought Taylor was over the whole Joe Jonas dumping her on the phone thing, she’s fucking not! This song is all about NYC, and at the time Joe was her only NYC-based boyfriend. You do the math.

1989, 2014

I think we have all had at least 2-3 good angry public cries to 1989 since the time it has come out. If not, you’re probably dead inside, and I commend you for it. This album was the nail in the coffin for Taylor’s “country girl” image as she went full pop star and honestly, we didn’t hate it. 1989 is full of amazing breakup tunes, but there’s actually a surprising lack of info regarding who each of these songs are about.

"Welcome To New York"
ABOUT: New York
WHO HE IS: The greatest city in the world.
THE EVIDENCE: New York City literally paid Taylor Swift to write a song about them, because there totally aren’t enough songs about New York. Hard to tell who is more desperate here.

"Blank Space"
ABOUT: ????
WHO HE IS: ????
THE EVIDENCE: I only put this here because, given that "Blank Space" is one of the biggest singles off the album, it’s kind of crazy we don’t know who this one is about. Could it be about Taylor's breakup with the public's favor, after we all wised up and realized she's fucking insane? That's just my theory. If you have any info re: "Blank Space"’s mystery man, please forward them to the Senate Intelligence Committee immediately. The people demand an investigation.

Blank Space

"Style"
ABOUT: Harry Styles
THE EVIDENCE: I mean, the song is called “Style.” Also, the lead in the music video looks exactly like him.

"Out Of The Woods"
ABOUT: Harry Styles, again
EVIDENCE: Harry Styles is the big winner for 1989. This song refers to paper airplanes, which is probably a reference to the matching paper plane necklaces Taylor and Harry had while they were together (barf), also she talks about “snowmobiles,” which is apparently something they did together.

"Bad Blood"
ABOUT: Katy Perry
WHO SHE IS: Hillary Clinton's campaign chairwoman/pop star with boobs.
EVIDENCE: I know they never dated, but Taylor Swift is literally obsessed with Katy Perry, so it’s almost like they did. Everyone knows this song is about Taylor’s feud with KP over John Mayer a backup dancer. And the whole girl gang music video thing was obviously an attempt to show Katy and the world who is more popular. Pettines Level: High.

Bad Blood

As you can see, Taylor Swift is both a lyrical genius, and a fucking delusional psychopath. Who has the time to hide so many clues in so many songs? But you know what they say, “the more batshit the betch, the better the pop album.” So how did everything shake out, numbers-wise? Congrats to Joe Jonas and Jake Gyllenhaal for tying for first place with 4 songs apiece. Honestly, you’re in incredible company. Though of course, they could always be knocked out of first if Taylor’s next album turns out to just be a 12 song manifesto about her relationship with Tom Hiddleston. Sounds horrible but, knowing Taylor, she’d find some way to make the whole thing catchy AF. 




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