Taylor Swift's Biggest Breakups: Gyllenhaal? Mayer? Kennedy? Harry Styles Isn't Alone

Word (and possibly a tweet) has it that the One Direction heartthrob has joined the growing ranks of Swift's ex-boyfriends—we run down her most infamous splits

By Natalie Finn, Rebecca Macatee Jan 08, 2013 12:50 AMTags
Taylor Swift , Harry StylesHumberto Carreno/startraksphoto.com

From X Factor to ex-factor, Taylor Swift and Harry Styles are said to be going in different directions.

The 23-year-old pop superstar and the 18-year-old One Direction heartthrob have reportedly split up after roughly two months of dating, just days after they shared a New Year's Eve kiss in frostbitten New York and flew off to the sunny Caribbean.

Stop us if you've heard this one, but...We're sensing a pattern here.

The Red artist rebounded, er, swiftly with Styles after breaking up with Conor Kennedy in October, spending her 23rd birthday with him in London and hitting the slopes in Utah together a few weeks ago. Styles even met Swift's mom!

Folks may have been slow to catch on, but on Friday it appears she participated in one of the hallowed rituals of the breakup process—she tweeted a Taylor Swift song lyric!

"...'til you put me down," she wrote, quoting her recent hit single "I Knew You Were Trouble." So, in hindsight...Did Swift know Styles was trouble when he walked in?

A rep for One Direction had no comment on the split reports and Swift's camp has not yet returned a request for comment.

Whatever happened—we should know more when her next album comes out—here's hoping Styles doesn't leave Swift too "Haunted."

With Styles reportedly taking his place in the pantheon, let's take a trip down memory lane and see who stands out in Swift's rapidly expanding hall of exes:

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1. John Mayer: Taylor collaborated with John on his 2009 song "Half of My Heart." From what pop culture has managed to piece together, it wasn't long after that the twosome began quietly dating, only to end. And from the sounds of things, not well. Flash to 2010, when Taylor released "Dear John," a scathing ballad trashing the eponymous man for playing "dark twisted games" with girls' hearts. 

In June 2012, Mayer, now 35, told Rolling Stone he was "really humiliated" by Taylor's song, which he (and the rest of the world) presumed to be about him. "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."

But the drama didn't end there, and when Glamour magazine brought up John's hurt feelings in a recent interview, Taylor refused to listen. "No! I don't want to know, I don't want to know," she said. "I put a high priority on staying happy, and I know what I can't handle."

She also said it was "presumptuous" of John to even assume "Dear John" was about him. "I never disclose who my songs are about," she stated. Well, sometimes you don't have to.


2. Jake Gyllenhaal: Who could forget Taylor and Jake's brief but intense romance back in late 2011? Whether they were giggling over ice cream or sipping maple syrup lattes in Brooklyn, this hip duo was anything but shy when it came to the PDAs. 

But before the year was up, Taylor and Jake had called it quits. Many have speculated that Taylor's new song (seeing the pattern here) "We Are Never Ever Getting Back Together" is about her handsome 31-year-old ex. Somehow we doubt Jake will pull a John and bring this up in his next interview, though, so we may never know for sure.

3. Joe Jonas: Here's a golden rule of dating: Never break up with someone on the phone. In 2008, Joe Jonas learned that lesson the hard (and very public) way, when Taylor put the boy bander on blast for doing just that. In an appearance on The Ellen DeGeneres Show, she said the kamikaze breakup call "was like, a record, I think, for how quick. I looked at the call log—it was like 27 seconds." If you listen closely, you can still, to this day, hear the audience's boos.

But now that some time has passed, Joe and Taylor's split seems to be water under the bridge. In a recent interview with 94.7 FM, the Jonas Brother insisted Taylor's "We Are Never Ever Getting Back Together" song was not written about him. "That said, I think the song is great," he added. "Taylor does pop music really well and I'm happy for her."

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4. Taylor Lautner: From October to December 2009, the Valentine's Day costars were reportedly so a couple. When Tay squared parted ways after Lautner's 19th birthday party, it was allegedly because "he liked her more than she liked him." 

And while we know she'll never explicitly confirm it, we're pretty sure Taylor's regretful 2010 song "Back to December" is about the Twilight star. "I miss your tan skin, your sweet smile," she sings wistfully. Her lyrics even suggest a reconciliation, but so far as we know, that's yet to happen.

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5. Cory Monteith: The Glee star and Taylor never confirmed their romance in 2010, though there's plenty of photographic evidence that they enjoyed spending solo time together. However, there don't appear to be any hard feelings, as in a recent interview on The Ellen DeGeneres Show, Taylor blushed when she was shown Cory's picture. After pointing out that she didn't date Justin Timberlake or Ashton Kutcher, she got quiet when it came to the 30-year-old singer-actor. "Mmm?" she said, quickly trying to change the topic. "What are you doing?!" 

Oh, just running through your romantic history, Taylor. Might be something to get used to.

(Originally published Oct. 26, 2012, at 6:05 a.m.)