17 Taylor Swift Songs That Prove She Will Never, Ever Kiss & Not Tell

Kiarra Sylvester | Aug 17, 2016 Celebrities

Taylor Swift

While I'm still torn on how I feel about Taylor Swift herself, I can't and absolutely won't deny that I can jam out to many of her songs. You see, I'm all for music that advocates never ever getting back together with exes. And, oddly enough, I can't wait to hear the tracks she pens when whatever's going on with Tom Hiddleston inevitably meets the same fate as her recent failed relationship with Calvin Harris did. We don't mean to be cruel, but even Taylor Lautner has confirmed that there's indeed a song about him. (Scroll through to number nine to get those deets.)

Although a great deal of the time Swift is teasing us with details and never fully indulging us with identities, it's become fun for us to name the crush she's exposing. That's why we couldn't resist capturing her paper trail of presumed ex-loves and those she pined over with this timeline of her music.


Images via Amazon

  • Tim McGraw


    At first you may think that the 2006 hit "Tim McGraw" is all about, well, Tim McGraw -- but nope! It's actually about one of Swift's high school boyfriends who was headed off to college. The singer recalled her first hit single (from her debut album Taylor Swift) in a sit-down with CMT:

    I got the idea in math class. I was just sitting there, and I started humming this melody. I kind of related it to this situation I was in. I was dating a guy who was about to go off to college. I knew we were going to break up. So I started thinking about all the things that I knew would remind him of me. Surprisingly, the first thing that came to mind was that my favorite country artist is Tim McGraw.

    So now you understand why the lyrics read: 

    But when you think Tim McGraw/I hope you think my favorite song/The one we danced to all night long/The moon like a spotlight on the lake.

  • Teardrops on My Guitar


    Okay, so maybe she name-drops more than we realized. In fact, the very first word to the song "Teardrops on My Guitar," featured on the album Taylor Swift, actually unveils the name of presumably just one of Swift's high school crushes: 

    Drew looks at me, I fake a smile so he won't see/That I want and I'm needing everything that we should be/I'll bet she's beautiful, that girl he talks about/And she's got everything that I have to live without.

    Drew Hardwick has often been named as the oblivious guy we all know, who talks you to death about his girlfriend and totally ignores your little heart eyes. Taylor is pretty much an open book on this track! However, she further confirmed the details of the song in a 2008 interview with Washington Post -- where she also revealed that Drew popped up on her at her house two years after the fact. 

    Sorry, dude, but that's not how this works. Too little, too late. 

  • Picture to Burn


    While nearly all Tay's early songs on her 2006 self-titled album were sweet odes to guys, "Picture to Burn" was one of the first scathing tracks on which she completely trashed an ex -- and little did we know then that it wouldn't be the last. Although Jordan Alford was far from famous, Taylor maybe exaggerated when she called him a "redneck heartbreak who's really bad lying" -- or at least that's the one part he's not willing to own up to, according to his wife Chelsea Alford in an interview with Daily MailOh, BTW, this is the person who helped inspire the song, as she was apparently the girl he cheated on Taylor with (and she was also friends with Tay) around 2004.

    Whoa! Well, thank God I wasn't the only one having a tough time in high school. 

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  • Should've Said No


    Taylor dated Sam Armstrong in 2004, but the only thing that we really know about it was that it was sorta DOA due to his thoughtless cheating. But, we're almost positive he learned his lesson after she basically slut shamed him for "letting it all go" in "Should've Said No" from her self-titled album.

  • Forever and Always


    Joe Jonas was T. Swift's first beau in the spotlight when they dated in '08, and inevitably her first heartbreak ... in the spotlight. While Taylor claimed that Jonas ended things over a 27-second phone call, he fired back and implied that Taylor was the one who ended the discussion. While none of the lyrics actually point to Joe, she did admit that at least one of the songs on her 2008 Fearless album is, indeed, about the singer. But, in the same way he was quick to fire back after claims of poor breakup etiquette, he and the Jonas brothers also penned a not-so-veiled song in response to Swift's, called "Forever and Now."

  • Holy Ground


    The proof for "Holy Ground" is all in the pudding ... and the timing. At this point in her career there were only two guys she'd experienced New York with, and since the wounds were still too fresh with Jake, it seems fitting that it's Joe Jonas whom she speaks of in the song. You know how it is when you get all nostalgic and start thinking back on old loves -- well, it seemed that was exactly what she was doing on her 2012 Red album, years after her quickie breakup with Jonas. 

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  • Hey Stephen


    While the two never actually dated, Taylor admitted that this song from her Fearless album was about a guy whom she had a crush on. However, we got all the confirmation we needed when singer for the band Love and Theft (which opened for her tour in 2008), Stephen Barker Lilestold Access Hollywood that he had never had a girl do something so nice for him before. And weirdly, like a couple of middles schoolers at their first dance, no one made a move -- even after Liles wrote a song for Taylor in return.

    But, then again, not all crushes are meant to be acted on. 

  • Enchanted


    Well, we don't have to do too much digging around for this one, as Owl City's Adam Young told US Weekly the story behind the song "Enchanted" (from the 2010 Speak Now album). The tune was apparently inspired by the fact that Young had used the word "enchanted" in an email and Taylor had never really heard it used before. He also admitted that he feels like he might be too small-time for the star ... so his uncertainty leaves us a little uncertain as to whether or not this crush could ever really take off. 

  • Back to December


    The Speak Now album actually goes down as the first time in history that Taylor Swift wrote a lyrical apology to an old beau. Based on the songs lyrics ("I miss your tanned skin, your sweet smile") and the nature of her relationship (with Taylor Lautner, reportedly, who was apparently more into her than she was him), and their November/December 2009 breakup, everyone assumed the Twilight star was the subject. Until recently all the evidence was speculative ... but then Lautner did us a solid and confirmed that the song is, in fact, about him.

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  • Dear John


    With a rather obvious name, we can only draw an equally obvious conclusion that this song was intended to shade the infamous Hollywood heart breaker John Mayer, whom she briefly dated at the end of 2009 and into 2010. Sure, we're fans of Taylor's taking her breakups to the bank, but John Mayer said he was "humiliated" by being the subject of her lyrical stroke of genius in the track "Dear John" (off her Speak Now album). I'm not sure I'd be a fan of anything that questioned my morals with lyrics like, "Dear John, I see it all, now it was wrong / Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" 

    But I will say that it almost seems hypocritical for Swift to throw the poor guy under the bus for dating younger women, when she continues to date guys around the same age as John (we're looking at you, Tom Hiddleston). 

  • Mine


    Although there was never any definitive proof that Taylor and Corey (who passed away in 2013) dated in '10, I think sometimes silence says waaay more than words (even the ones featured on the Speak Now album). And so when Tay went on the Ellen Show in 2012 and went completely mum when asked about her relationship with the late Cory (after making quite a bit of noise over her other relationships), it pretty much confirmed some sort of something. What's more is that the song "Mine" (about a crush that made her instantly dream about the future) was penned around the time that the two were often seen photographed together. So, there it is. 

  • All Too Well


    In this sweet track "All Too Well" found on Red, the hints to Jake Gyllenhaal aren't so subtle, as she makes references to autumn leaves and spending time at her mysterious suitor's sister's house -- which the two reportedly did during Thanksgiving in 2010

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  • We Are Never Ever Getting Back Together


    Many outlets have credited Jake Gyllenhaal as the inspo that brought us this 2012 scathing summer anthem (and a few more on Red) due to the video visuals where Swift warms up with her date's scarf -- a scarf and scenario all too real for it not to be symbolic. (A source also apparently confirmed this to US Weekly.) But, more tellingly, I must also point out that they guy in the video may resemble Jake -- just a little. 

  • Begin Again


    There's been a ton of indefinite speculation over who the 2012 song "Begin Again" may be about, so we did a little digging and this song is definitely about two people -- and in it, Swift sounds like she's on the cusp of a breakup and meeting someone new (the breakup being with Jake Gyllenhaal and new guy being Conor Kennedy, whom she dated in 2012 not too long after Gyllenhaal). Many of the lyrics point to the transitional relationship as Tay sings, "I've been spending the last eight months thinking all love ever does is break and burn and end" -- which is approximately how long she had been done with Jake before we found out about Conor. Another tell-tale lyric that speaks to Jake: "Turn the lock and put my headphones on, he always said he didn't get this song." She calls out Jake (supposedly) in "We Are Never Getting Back Together" for placing his indie music on a pedestal (over her music, that is). 

    Has anyone nominated Red for album most likely to throw shade yet? We should consider it.

  • I Knew You Were Trouble


    Another summer anthem, indeed. This one off of the Red album was immediately rumored to be about One Direction bad boy Harry Styles. And although I had my doubts due to some lyrical overlaps, Taylor herself confirmed that this song was about him in her interview with UK's Times Magazine, saying, "It's not hard to access that emotion when the person the song is directed at is standing by the side of the stage watching." And yes, Styles was certainly present at the Brit awards when she rocked the stage with this song in 2013.

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  • Style


    Obvi this is also about her short time with Harry Styles back in late 2012 and early 2013. But in case the song title doesn't give it away, then perhaps it's that practically every other song featured on 1989 seems Harry-inspired. The telling lyrics from "Style"?

    You got that long hair, slicked back, white T-shirt/And I got that good girl faith and a tight little skirt/And when we go crashing down, we come back every time/'Cause we never go out of style

    But, the best part is how One Direction sorta wrote a tune of its own that definitely responded to the song, with Styles also admitting that he's essentially the right kind of wrong. (No worries, Tay. We all think we can make the bad guys good for a weekend.) 

  • Out of the Woods


    This song on her 1989 album had a ton of symbolic references to the singer's fleeting romance with Harry Styles. Here's the quick rundown of revealing lyrics:  1) "Looking at it now, last December": This is reportedly when the couple broke up. 2) "Your necklace hanging from my neck ... Two paper airplanes flying, flying, flying": This is a reference to the matching airplane necklaces that the couple had. 3) Last but not least are the lyrics that read, "Remember when you hit the brakes too soon/Twenty stitches in a hospital room": That so obviously point to the ski accident that she spoke of in her cover for Rolling Stone.

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