Many of Taylor Swift’s most famous songs are diss tracks about ex-boyfriends. From high school sweethearts who paid the price for doing her wrong and taught her to turn her pain into art, to recent boyfriends Joe Alwyn and Matty Healy.
Today, we take a look back at Taylor’s dating history, the songs that ex-flames like Joe Jonas, Taylor Lautner, Jake Gyllenhaal, Harry Styles, and Tom Hiddleston inspired, and why they are never, ever, ever, getting back together.
Jordan Alford
Taylor Swift’s first major schoolgirl crush was Jordan Alford. They dated during their freshman year at Hendersonville High School in Tennessee.
Everything was hunky dory until Alford started seeing another girl called Chelsea, who happened to be a close friend of Taylor’s.
Chelsea said of Taylor, “We were kind of good friends at school, later… not so much.” Swift called Alford “narcissistic”
but he helped her learn to channel her emotions into songwriting, so we have him to thank for Taylor Swift’s first breakup burn track.
Picture to Burn
Taylor and Jordan’s split prompted her to write “Picture to Burn” about him. It was one of her first collaborations with co-writer Liz Rose and appeared on her self-titled debut album.
The lyrics include, “I hate that stupid old pickup truck you never let me drive / You’re a redneck heartbreak who’s really bad at lying / So watch me strike a match on all my wasted time / As far as I’m concerned, you’re just another picture to burn.”
Jordan Alford later denied he was a redneck… and he married Chelsea!
Brandon Borello
Taylor Swift and Brandon Borello were also high school sweethearts. However, the romance was doomed as Brandon had to move away for college.
Taylor was heartbroken at the thought of being abandoned and wrote two songs about Borello. Surprisingly, both tracks were actually quite nice.
Swift first performed “Our Song” at her school talent show. But where did Taylor write it? Well, as any Swiftie knows, she “
was ridin’ shotgun with my hair undone, in the front seat of his car. I grabbed a pen and an old napkin. And I wrote down our song.”
Tim McGraw
After Brandon callously abandoned Taylor to go to university, the devastated songwriter penned “Tim McGraw”
with Liz Rose for her self-titled debut studio album. She explained, “It was with this guy I was dating, and he was about to go off to college, and I was thinking about all the things that I knew would remind him of me.”
Taylor told USA Today in 2006 that Brandon bought her first album and “really loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.”
Sam Armstrong
With Brandon’s departure to college, young Taylor soon moved on to Sam Armstrong. While still in high school, she fell head over heels for the lucky young man.
But the romance crashed and burned as Taylor soon discovered Sam had also been seeing another girl behind her back.
She definitely knows how to pick ’em!
Sam Armstrong’s transgression saw him go down in history. This was the boyfriend who helped Taylor Swift perfect her trademark and winning formula of breakup burn songs.
Should’ve Said No
From Tammy Wynette to Dolly Parton, female country artists famously unleash their feelings through their music.
And when Taylor ditched Sam for cheating, she didn’t hold back! The lyrics for “Should’ve Said No” include the lines, “
You say that you’d take it all back / given one chance / It was a moment of weakness / and you said ‘Yes.’”
The song’s title comes into play with the line, “I shouldn’t be asking myself, ‘Why?’ You shouldn’t be begging for forgiveness at my feet.
You should’ve said ‘No,’ baby, and you might still have me.”
Joe Jonas
T-Swizzle’s first famous boyfriend was Joe Jonas, whom she met while supporting the Jonas Brothers on their Burnin’ Up tour.
They began dating in July 2008, and the media lapped up their relationship. For a hot minute, they were seen everywhere together.
But then, after just three short months, in October 2008, Joe dumped Taylor in the worst way imaginable, spurring Swift to scribe a squadron of songs throwing shade at Joe.
And when you find out how he kicked her to the curb, you’ll agree that he deserved it.
Forever and Always
Joe dumped Tay in a 27-second phone call. Ouch! She says “Forever and Always” is about “watching somebody completely fade away in a relationship and wondering what you did wrong.”
“Last Kiss” and “Holy Ground” are also about Jonas.
In 2009, Swift hosted Saturday Night Live and said, “You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing really well, and I’m hosting SNL!”
Lucas Till
Taylor met Hollywood heartthrob Lucas Till when they both appeared in Hannah Montana: The Movie. Lucas played Miley Cyrus’s love interest while Taylor made a cameo and performed her song “Crazier.” They dated while filming the movie between April and May 2009, before realizing they were better suited as friends.
At the time, Lucas said, “We just really both liked each other…[but] most relationships work out ’cause you get along and then you don’t, and then you makeup, and it’s passionate.”
However, this romance was devoid of passion.
You Belong With Me
After Lucas McGyvered his way out of the relationship, he told MTV, “We dated for a little bit. But there was no friction because we were too nice; I really just liked her as a friend. That’s the only reason that didn’t work out.” For once, Taylor didn’t write a song about this breakup.
You can’t turn your pain into art if it doesn’t hurt. Right, Swifties? However, Lucas Till did appear in her “You Belong With Me”
music video in 2009. He won her heart by playing the next-door neighbor. Awww!
Taylor Lautner
The year was 2009, and the Twilight saga had reached a fever pitch. Then, on a dark, autumn night, a young chanteuse named Taylor bumped into a hunky young werewolf also named Taylor. Luckily, it wasn’t a full moon, so she didn’t get eaten. In fact, the two Taylors met when they co-starred in the rom-com Valentine’s Day.
Yes, folks, this was the famous Taylor and Taylor relationship the tabloids had been waiting for! Now, if only they could think of a witty portmanteau… The witty portmanteau they came up with was Taylor/Taylor.
Back to December
The whirlwind werewolf romance only lasted a couple of months. After they went their separate ways, Taylor 1.0 wrote about Taylor 2.0.
In 2016, the handsome actor revealed that Swift’s hit “Back to December” was actually about him.
In the lyrics, Swift wrote, “Your tanned skin, your sweet smile.” The song also goes on to apologize for a rough night in December.
That, you see, is the fateful night she dumped him. When asked what he thought of the song, Lautner mused, “That’s what she does.”
John Mayer
Next on Taylor’s never-ending list of boyfriends is fellow singer-songwriter John Mayer. The then-32-year-old musician dated Swift when she was 19.
While their age gap made headlines, their relationship is remembered to this day for their back and forth of diss tracks.
In a 2012 Rolling Stone interview, Mayer revealed that one of Taylor’s songs about him “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.”
Dear John
The song in question was “Dear John,” in which Swift opines, “I see it all, now it was wrong / Don’t you think nineteen is too young / To be played by your dark, twisted games when I loved you so?”
Mayer responded with “Paper Dolls,” which includes the lyrics, “Don’t you think I was too young to be messed with?
The girl in the dress cried the whole way home / I should’ve known.” He also wrote “Still Feel Like Your Man”
about Swift and called her songwriting “cheap.”
Corey Monteith
Taylor Swift and Cory Monteith supposedly dated in the spring of 2010. The Canadian actor and musician was most famous for playing Finn Hudson in the musical comedy-drama TV show Glee. They were first spotted and photographed together at a Grammys afterparty. They hung out loads, spending time together at a Hollywood bowling alley.
In May 2010, Ellen DeGeneres asked Monteith if they were dating. “No, we’re just friends,” he replied.
When Degeneres said he and Swift would make a “cute couple,” Monteith responded, “She’s lovely.”
Mine
Depending on who you believe, Taylor dated Cory for a few weeks, or they were just good friends. Whichever it was, he had a lasting effect on Taylor and she wrote a song about him. In the track “Mine” from the album Speak Now, Swift sings about how she really liked a boy she barely knew.
Swifties say that boy is Corey, and the song goes on to state that he tried to take their relationship to the next level.
Sadly, Corey passed away in July 2013.
Jake Gyllenhaal
We have mutual friend and matchmaker Gwyneth Paltrow to thank for introducing Taylor to actor Jake Gyllenhaal. The pair were first spotted together backstage at Saturday Night Live in October 2010.
They were often spotted painting the town red in New York City and Los Angeles, and gossip magazines soon proclaimed they were in love.
But once again, there was a significant age gap. Jake is 10 years older than Tay, and he felt the relationship wasn’t working due to the age gap.
We Are Never Ever Getting Back Together
After three months, Jake called it quits. “We Are Never Ever Getting Back Together” reportedly celebrates Tay finally feeling free after her draining on-and-off relationship with Jake.
It cites Gyllenhaal’s snobby music taste and wishy-washy feelings. She even hired a Jake look-a-like to play her love interest in the video.
“All Too Well” documents a road trip to upstate New York, a Thanksgiving dinner at Jake’s sister Maggie’s house, and the fact that Jake still wears Taylor’s scarf to this day!
“I Bet You Think About Me” is another arrow fired at Jake.
Conor Kennedy
After Jake, she dated Conor Kennedy during the summer of 2012. There were some raised eyebrows as she was 22 and he was an 18-year-old high school senior.
After weeks of dating, he got spooked when she bought a $5 million house next door to the Kennedy compound in Massachusetts.
An insider told Radar, “Conor’s just an 18-year-old kid and wasn’t ready for anything super serious. But Taylor is looking for her soulmate, and it kind of freaked him out with how strong she came on.”
Begin Again
Conor bailed and Taylor was heartbroken. But she still managed to milk three songs out of the short relationship. “Starlight” and “
Everything Has Changed” are about Kennedy. In “Begin Again,” she compares the relationships between Jake and Conor.
The lyrics go, “As you throw your head back laughing like a little kid / 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.”
Harry Styles
When Harry met Taylor at The Kids’ Choice Awards in March 2012, the chemistry was plain for all to see.
But it took the pair until December to officially get together. Known by the portmanteau “Haylor,”
they were snapped strolling through Central Park, at the zoo, kissing in Times Square on New Year’s Eve, and even got in a snowmobile accident.
However, after a “rocky Caribbean vacation,” the relationship was only ever headed in one direction – downwards.
I Knew You Were Trouble
Harry called things off, and T-Swizzle was left heartbroken. She channeled the pain of a month-long relationship into three new songs. “
I Knew You Were Trouble” is about Harry and directly references their Caribbean holiday with the lyrics, “
Cause I knew you were trouble when you walked in / So shame on me now, Flew me to places I’d never been / ‘Til you put me down, oh.”
Taylor’s album 1989 is filled with references to Harry Styles, especially “Out of the Woods,” which mentions their December romance and snowmobile accident. “Style” needs no explanation.
Calvin Harris
Next, Taylor dated Scottish musician and DJ Calvin Harris for 15 months. “Tayvin” met in February 2015, at the Elle Style Awards, but didn’t start dating until March. Shortly after their first anniversary, she gushed to Vogue magazine, saying, “I’m in a magical relationship right now.”
She continued, “And of course, I want it to be ours, and low-key … this is the one thing that’s been mine about my personal life.”
However, on June 1st, 2016, “Tayvin” announced they’d split amid rumors Taylor had found another man to get over her highland fling.
Tom Hiddleston
Next, Taylor Swift began a secret romance with English actor Tom Hiddleston. It was the worst-kept secret ever. They met at New York’s Met Gala, and just two weeks after splitting with Calvin Harris, British newspapers ran pics of Taylor and Tom kissing. The Loki actor told The Hollywood Reporter, “Taylor Swift and I are together, and we’re very happy. It’s not a publicity stunt.”
“Hiddleswift” or “Tiddleston” were spotted in England, Rhode Island, Italy, Australia, and Tom was even photographed wearing an “I Heart T.
S.” T-shirt. But their relationship was soon on the rocks.
Getaway Car
The passionate, whirlwind romance between Taylor and Tom lasted just three months. After the breakup, Swift offered up the most devastating song on her 2017 album Reputation. However, “Getaway Car” is not just about Tom Hiddlestone… it’s also about Calvin Harris.
The lyrics suggest that Taylor used Tom as a rebound. She used him as a metaphorical getaway car to get over Calvin.
The first few weeks with him were fun, but the relationship eventually ran out of gas.
