Top 10 Taylor Swift Songs About Exes

Top 10 Taylor Swift Songs About Exes

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If you’re a Swiftie ex, well, you can expect to be swiftly addressed in song. Join MsMojo as we count down our picks for the Top 10 Taylor Swift Songs About Exes. For this list, we’re focusing on all the exes of Taylor, whether they be superstars, millionaires or just regular dudes. We’re excluding subjects of her songs that aren’t exes¬-– at least that we know of – like Katy Perry, but rather the rumored inspiration behind “Bad Blood.” Oh, and no Eddie Redmayne either, because that’s more of a rumor than a documented relationship.

#10: “Tim McGraw” (2006) Drew Dunlap

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When you’re a high school freshman, the smallest of things have a way of swaying your thoughts. In this case, it was a country singer that reminded Taylor Swift of her future ex-boyfriend – high school senior Drew Dunlap. On the one hand, you’ve got to bow down to Taylor for embracing her artistry at such a young age; but on the other, it only makes sense to question the intensity of the relationship if the girl’s already working on a breakup song for her debut single. But hey, that how’s it goes – sometimes a guy’s gotta leave for college, and sometimes a girl needs inspiration.

#9: “The Last Time” feat. Gary Lightbody (2012) Jake Gyllenhaal

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With fame comes opportunity, and with opportunity comes…well, less opportunity for enduring relationships¬– at least when both parties involved are at the height of their careers. In late 2010, Taylor embarked on a brief romance with the tough guy/nice guy Jake Gyllenhaal, but according to reports, he didn’t exactly keep his woman at the top of his to-do list. We can’t blame Taylor for taking offense, but…such an experience did provide the foundation for yet another hit. And let’s keep it real – Taylor will only be as single as she chooses to be.

#8: “Mine” (2010) Cory Monteith

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The late Cory Monteith will always be best known for his work on the television series “Glee.” However, shortly after joining the cast as Finn Hudson, he was often linked to Taylor, as Ellen DeGeneres so gently alluded to on her show. And so, just the idea of a lasting romance with Cory must’ve left a mark on Taylor, as her apparent ode to the would-be relationship served as the lead single for her third studio album. Neither of the two ever confirmed the suspicions, but it’s clear there was definitely a shared feeling of respect and admiration.

What’s the most logical way to deal with unrequited love when you’re a teenager? Well, naturally, you question the guy’s sexuality, or at least pretend to, and then proceed to record your thoughts for a country smash hit. To be fair, Taylor has admitted that “Picture to Burn” doesn’t necessarily reflect a mature style of writing, but given the tongue-in-cheek shots at Jordan Alford, who later married one of Taylor’s friends, well, you can’t help but laugh. Back in 2006, “Picture to Burn” endeared the rising star to young girls everywhere, even if she had to throw ol’ Jordan under the bus.

#6: “Should’ve Said No” (2006) Sam Armstrong

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Ah…remember the days of Taylor and Sam Armstrong? No? Okay, so nobody ever gave much thought to Mr. Armstrong, but that's only because nobody in the realm of pop culture even knew who the frig he was. According to reports, this guy cheated on our girl Taylor when she was 16, and given the intensity of “Should’ve Said No,” the singer must’ve really let that dude have it. In the end, it only made sense to travel the high road, because, well, wouldn’t most guys love to know that a pop star wrote a song about them?

When you’re a country girl growing up in Tennessee, you date the country guys of Tennessee. However, after Taylor became a household name, she was able to broaden her horizons, so to speak. By which we mean, she hooked up with Conor Kennedy, son of Robert F. Kennedy, Jr. With “Begin Again,” Taylor Swift could now approach songwriting from a different angle, as the young Kennedy was just a teenage kid when the two were linked during the summer of 2012. Beyond all the fortune and fame, it’s evident that Taylor just wanted someone to “get her” – not a cocky kid who only wanted to get some.

#4: “Holy Ground” (2012) Joe Jonas

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When you enter a relationship with Taylor Swift, chances are that you’ll become the focus of at least one future hit, but in the case of Joe Jonas, Taylor Swift wasn’t exactly done with him. Then again, “Holy Ground” isn’t exactly a takedown like the less-than-subtle “Forever And Always,” as Taylor had years to reflect after the 2008 break-up and subsequently wrote a level-headed song about the joys and frustration of a public romance. It’s not one of her most commercially successful songs, however, the lyrics reflect a woman in touch with her individuality and a new outlook on life.

#3: “Back to December” (2010) Taylor Lautner

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Every now and then, a true artist must take a look at themselves in the mirror and try to imagine the pain that they might’ve been inflicted on others along the way. Less than a year after breaking up with actor Taylor Lautner in December of 2009, Swift released an apology ballad in which she offers some small talk in the open before moving on to more important matters. You know, like “sorry, for breaking your heart and killing your roses.” The two have remained mum on the specifics but the title might as well have been called “Back to December of Last Year When I Broke Up with the Other Taylor Named Taylor Lautner.”

#2: “I Knew You Were Trouble” (2012) Harry Styles

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With all due respect to Mr. Harry Styles, he can occasionally demonstrate Justin Bieber levels of douchebaggery. Sadly, young women can be tempted by that faux bravado, as was the case for Taylor when she boarded the Harry train¬– which unsurprisingly derailed just a few months later. What can you do when you’re as famous as Taylor and encounter such a uniquely bizarre individual as Harry Styles? Even Taylor couldn’t necessarily explain what happened, she was just drawn in. That type of crazy love involving two mega-celebrities nearly always provides the necessary inspiration for a Billboard hit.

#1: “Dear John” (2010) John Mayer

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In Taylor Swift’s short yet already legendary career, she’s dated a number of talented artists, and to be honest, the specifics are usually none of our business…at least until she makes it everyone’s business. With “Dear John,” Taylor wasn’t exactly vague with who the song was about, and given the extensive, lyrical breakdown of “John” taking advantage of a naïve teenager, it doesn’t come as a surprise that Mr. Mayer opened up to Rolling Stone about his thoughts on the production. Hey, we’re not picking sides, but when it comes to bitter Taylor Swift songs about her exes, there’s simply nothing quite like “Dear John.” So, do you agree with our selections? What is your favorite Taylor Swift song about an ex? For more mind-blowing Top 10s published daily, be sure to subscribe to MsMojo.