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Tim Tebow, Taylor Lautner & More Past Taylor Swift Boyfriends

Is country star Taylor Swift dating football hero Tim Tebow? From Joe Jonas to Jake Gyllenhaal, see photos of her past flames.

Recent Vogue cover girl and awards-sweeping country star Taylor Swift has been spotted at dinner with football hero Tim Tebow. From the time she broke Taylor Lautner’s heart to her rocky relationship with musician John Mayer, see photos of Taylor’s most famous flames.

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Tim Tebow

Country crooner Taylor Swift is known for her squeaky-clean, wholesome image—so a budding romance between her and famously religious football hero Tim Tebow seems to us like a match made in heaven. The two were spotted having dinner together Monday at the Toscanova Italian restaurant in Los Angeles’s Century City mall, where Tebow reportedly looked “more than happy to be talking with her.” Rumors of romance may turn out to be a bit premature, though—sources told ClevverNews that the duo may have been accompanied by their agents, suggesting the meeting was more business than romance. But as long as Tebow refrained from abruptly, well, Tebowing in the middle of dinner, we think he’s still got a shot.

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Taylor Lautner

Taylor Swift and Taylor Lautner became an item sometime during summer 2009, after costarring in the ensemble romantic comedy Valentine’s Day. But the Taylor-on-Taylor romance wasn’t meant to be, and things fell apart by year’s end. Their relationship is now famously chronicled in Swift’s song “Back to December,” in which the singer (with a penchant for publicly turning ex-boyfriends into hit singles) apologizes for breaking the Twilight star’s heart: “This is me swallowing my pride/Standing in front of you saying I’m sorry for that night/And I go back to December all the time.” Swift also describes Lautner’s “tan skin” and “sweet smile” (stomping out any doubt about who the song was for) and promises that “if we could love again, I swear I’d love you right.” When she performed the song at the 2010 American Music Awards, however, she ended it with a cover of the chorus from One Republic’s hit “Apologize,” subtly changing the lyrics to “He said it’s too late to apologize.” Guess our country cutie got shut down.

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John Mayer

Swift may have broken the heart of her fellow Taylor (Lautner), but when it came to her relationship with singer John Mayer, she apparently was the dumpee. After the two recorded a duet (sweetly entitled “Half of My Heart”) for Mayer’s 2009 album, Battle Studies, the pair started being spotted out together, even reportedly staying at the same hotels. The 12-year age difference was enough to give many the heebie-jeebies (Taylor was just a year out of high school at the time!), but the romance was never confirmed—that is, not until Swift’s song “Dear John” hit the airwaves. In it, she bemoans some of the relationship’s roughest parts: “I lived in your chess game, but you changed the rules every day/Wondering which version of you I might get on the phone tonight/Well, I stopped picking up, and this song is to let you know why.” The song seems to have struck a chord with Mayer: he’s recently been reported to have released an apology song to Taylor called “Speak for Me.”

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Adam Young

On the opposite end of the douche-bag spectrum from Mayer, however, was Adam Young, the electronica artist perhaps better known as Owl City. He and Swift reportedly met at a party in New York City, and she later revealed to Yahoo Music that the inevitable song she wrote about the encounter (entitled “Enchanted”) was about “pining away for if you're ever going to see someone again, walking away too early … and meeting him, it was just this overwhelming feeling of: I really hope that you're not in love with somebody.” Young eventually caught on and—just in time for Valentine’s Day 2011—released a cover of Taylor’s song, tweaking the lyrics to say, “Oh, Taylor, I was so enchanted to meet you too.” In an interview with Us, Young continued to gush about his crush on Taylor: “She's a superstar, and I'm just this kid from a small town in the middle of nowhere, so I feel like that peasant in the midst of a princess and that whole classic story.” Unfortunately, Young also added in the interview, “I never heard back from Taylor, but I’m sure she’s busy.”

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Joe Jonas

The then-17-year-old country crooner cozied up to Disney star Joe Jonas in 2007. The relationship, which ended sometime in 2008, apparently was terminated by Jonas in a very brief phone call. Swift recalled their relationship on The Ellen DeGeneres Show and said, “I'm not going to remember the boy who broke up with me over the phone in 25 seconds when I was 18 ... I looked at the call log—it was like 27 seconds. That's got to be a record.” Of course, Taylor had the final say in the form of much-publicized song lyrics: In the ironically titled “Forever and Always,” Swift sings, “Did I say something way too honest/Make you run and hide/Like a scared little boy?” In the 2010 song “Better Than Revenge,” Swift also allegedly went on to trash the girl who “stole” the Jonas brother away from her, actress Camilla Belle. “She’s not a saint, and she’s not what you think. She’s an actress/She’s better known for the things she does on the mattress,” Swift sings.

Toby Hemingway

In the summer of 2010, Swift and her “Mine” music-video costar Toby Hemingway were spotted spending time together in Los Angeles and Maine. Swift’s reps wouldn’t confirm or deny the relationship, but from the looks of his Facebook page pictures, Hemingway was bad news. Seen partying, drinking, smoking, and cuddling up with other women, Hemingway didn’t scream perfect for our down-to-earth country star.

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Cory Monteith

Glee leading man Corey Monteith was seen canoodling with Swift in January 2010. Although neither confirmed the short-lived relationship, was Monteith the inspiration for her single “Mine”? Swift revealed to MTV that the song is “a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes, almost like a weird science-fiction movie.” She added, “After I wrote the song, things sort of fell apart, as things so often do.”

Lucas Till

Before he starred in Swift’s “You Belong With Me” music video, Lucas Till could be seen in Hannah Montana: The Movie, in which Swift makes a cameo. Sharing a romantic interest with both ladies in different mediums, Till spills that Swift is the better kisser. But did the pair share an off-screen romance? According to Till, yes. He told MTV that they dated briefly after shooting the music video, but things soon fizzled out because there wasn’t any passion. “With us I really just liked her as a friend. That’s the only reason that didn't work out.”

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Stephen Barker Liles

Before Swift ever canoodled with a Jonas brother, a werewolf, or assorted music-video studs, there was Stephen Barker Liles, singer for the Nashville-based pop group Love and Theft. The pair first met backstage at an event in 2007 and got to know each other better when his band opened for Taylor’s act on a few tour dates in 2008. Though the two were never officially a couple, Taylor still found enough inspiration in her crush to pen a song called “Hey Stephen” for her 2008 album Fearless. In it, she croons, “Hey, Stephen, I could give you 50 reasons why I should be the one you choose/All those other girls, well, they’re beautiful—but would they write a song for you?” Liles told People in 2008, “It’s totally flattering to have somebody write a song like that for you,” though a source in Swift’s camp insisted to the magazine that the two never dated. “It was a brief crush—nothing more.”

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Jake Gyllenhaal

The nine-year age difference didn’t seem to be a problem for then 30-year-old Jake Gyllenhaal and 21-year-old Swift (it was, after all, less cringeworthy than the 12-year difference between Swift and her former beau John Mayer). The pair were first seen together in October 2010, hanging out backstage at a Saturday Night Live taping and later having brunch in Brooklyn. But the romance didn’t last long, as the two were separated before the new year and spent their birthdays apart. Unfortunately for her fans, the relationship came after Speak Now was released, so no song (that we know of) has been inspired from her fling with the Brokeback Mountain star.

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Taylor Swift Super Fan: Kevin McGuire

Though Taylor’s made some screwy dating choices in the past, no one can dispute the goodheartedness of her most recent official choice: after an immense Facebook campaign to get Swift to go to the prom with a Somerdale, N.J., high-school senior named Kevin McGuire, who was diagnosed with leukemia when he was 13, the country star did the unexpected and actually replied. In a Feb. 24 Facebook post, she wrote, “Kevin, I'm so sorry but I won't be able to make it to your prom. But I was wondering, the ACM Awards are coming up.. Would you be my date? Love, Taylor.” The 18-year-old McGuire of course happily accepted, and the two are set to arrive at the Academy of Country Music Awards arm in arm on April 1.