Celebrities

5 Famous Guys Who Left Taylor Swift Completely Heartbroken

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Taylor Swift is BEYOND happy with Calvin Harris now, but the “New Romantics” singer had a long and rocky relationship history before finding happiness with the DJ. Since she first stepped onto the music scene back in the mid-2000s with her long, curly locks, Tay has had her fair share of rough breakups.

Sure, some of the former country star’s exes are supportive of her now, but they weren’t always on good terms with the singer. Even though Taylor’s past relationships have served as inspiration for her biggest hits (thank goodness for them, ya know?), they were also a major source of heartbreak for her, even if the guy’s intention was not to do so. Curious to know which famous faces left the 26 year old completely brokenhearted? Scroll down for all the deets!

1. Joe Jonas — We’re sure that by now everyone knows about the infamous 27-second breakup that happened over the phone between Joe and Taylor. Even though the pair didn’t date for too long, the blonde was just 18 at the time and his diss hit her hard. LBH, if Taylor was willing to put her heart into their relationship, the JoBro guy should’ve had the courtesy to end things in person. In the long run, however, the split benefited Taylor; without it, Swifties would’ve never gotten “Last Kiss” and “Forever and Always,” some of her BEST songs of all time!

Photo: Charlie Steffens/WENN

Photo: Charlie Steffens/WENN

2. Lucas Till — Lucas and Taylor met on the set her of “You Belong With Me” video, and the two actually had feelings for each other IRL. In an interview, Lucas admitted that they did, in fact, date briefly, but the relaysh was short lived because he realized he liked her only as a pal. “With us I really just liked her as a friend. That’s the only reason that didn’t work out,” the actor said. Ugh, being friendzoned is never easy… even when you’re a famous singer!

Photo: Nicky Nelson/WENN

Photo: Nicky Nelson/WENN

3. John Mayer — Who could forget this disastrous relationship? The idea of Tay and John being together may have seemed like a good idea at first, since they’re both talented singer-songwriters, but this pair was far from perfect. In “Dear John,” Taylor held nothing back when singing about the terrible relationship. “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,” Taylor sings in the interestingly named song. Tay then continued, “Well maybe it’s me and my blind optimism to blame / Maybe it’s you and your sick need to give love then take it away.” Eeek! Not good.

Photo: Brian To/WENN

Photo: Brian To/WENN

4. Jake Gyllenhaal — Jake is another one of Taylor’s exes who didn’t have the courtesy to end their relationship in person — he called it quits with her over the phone. Even though they seemed happy as ever when they were together, the actor apparently could handle all the attention that went along with being in a relationship with one of the biggest stars in Hollywood. He also felt as though their 9-year age gap was putting a strain on the romance. After suffering with her heartbreak personally for quite some time, the songstress then decided to channel her emotions in many heart-wrenching tunes on Red.

Photo: Dennis Van Tine/WENN

Photo: Dennis Van Tine/WENN

5. Harry Styles — We all adore Harry, but LBH — he DID leave Taylor feeling heartbroken. While it’s unclear as to who ended things, one thing we know for sure is that she wrote several songs about the Brit following their split. In the past, the 26 year old hinted that her “I Knew You Were Trouble” Brit Awards performance was was inspired by her relaysh with the 1D singer. When talking about her performance, Taylor explained that it wasn’t difficult too channel her feelings into it. “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,” she said. To add to that, in an interview with Elle, Taylor admitted that she was walking through London once, and suddenly thought about her ex. “A heartbroken person is unlike any other person. Their time moves at a completely different pace than ours. It’s this mental, physical, emotional ache and feeling so conflicted. Nothing distracts you from it,” she told the mag. Once Taylor got over the breakup, she wrote the 1989 track “Clean.”

Photo: WENN

Photo: WENN

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Those aren’t the only famous faces T. Swift has dated. These guys have also, quote-unquote, dated Taylor:

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