Taylor Swift’s Ex Files: The Ultimate Guide on Her Former Boyfriends and Break Ups

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Harry Styles is the latest guy to enter Taylor Swift’s world of ex-boyfriends.

After dating for two months, Life & Style exclusively revealed Taylor and Harry’s break up on Jan. 7.

EXCLUSIVE: Taylor Swift and Harry Styles break up

And now we’re looking back at all her other former partners — who’ve definitely inspired some of Taylor’s No. 1 hits over the years — and why love just wasn’t enough for them!

"The way I look at love is you have to follow it, and fall hard, if you fall hard. You have to forget about what everyone else thinks,” the 23-year-old's said. "It has to be an us-against-the-world mentality. You have to make it work by prioritizing it, and by falling in love really fast, without thinking too hard. If I think too hard about a relationship I'll talk myself out of it. ...I have rules for a lot of areas of my life. Love is not going to be one of them."

Joe Jonas (2008): Though the pair, both 19 at the time, kept pretty quiet about their short-lived relationship, their split became massive news when he reportedly dumped her on a 27-second phone call!
Song: “Forever and Always”
Taylor on break up: “I’ve written about [the split], and I like to write about my life … that’s just how I deal with things. [Forever and Always is] a song about watching somebody completely fade away in a relationship and wondering what you did wrong.”

Taylor Lautner (2009): The duo started dating after meeting on set of the flick Valentine’s Day. Swift was 20 and Lautner was 17. After dating just three months, they called it quits in December 2009.
Songs: “The Story of Us” and “Back to December” – which is apparently about Swift apologizing to Lautner for their split.
Swift reacts to seeing Lautner for the first time post-break up (though it’s not 100% confirmed it’s about him, who else could it be?!): “It was at an awards show and there had been this falling-out between me and this guy. I think both of us had so much that we wanted to say, but we’re sitting six seats away from each other, just fighting this silent war of ‘I don’t care that you’re here.’ I remember getting home and sitting at the kitchen table and saying to my mom, ‘It was like I was standing alone in a crowded room.’ That’s when my eyes glazed over and I got distracted and walked away to write [“The Story of Us”]. My mom is used to me doing that.”

John Mayer (2010): John and Taylor were rumored to be dating from late 2009 (after the Lautner split) until June 2010. Though Taylor sang on John’s hit “Half of My Heart,” it wasn’t enough to keep this pair together. Perhaps their massive age difference was to blame: he was 32, she was 21.
Song: “Dear John” (“Dear John, I see it all now that you’re gone / Don’t think I was too young to be messed with?”)
Taylor’s response to John’s quotes about “Dear John” – which he says he was “humiliated” by: “How presumptuous! I never disclose who my songs are about.”

Jake Gyllenhaal (2011): Jake, 29, and Taylor, 21 (at the time) shocked the world when they were photographed hanging out everywhere from Thanksgiving Day in NYC to her home in Nashville, but they split in December after dating two months.
Songs: A ton off her "Red Album" are said to be about him! “All Too Well” (“Left my scarf there at your sister’s house / And you still got it in your drawer even now)
Taylor on the song, though she won’t admit it’s about Jake: “[It] was the hardest to write because it took me a long time to filter through everything I wanted to say … It started out being a 10-minute song, which you can’t put on an album. I had to filter it down to a story that could work in the form of a song.”

Conor Kennedy (2012): After a summer of love — and hanging with Conor’s famous family — Taylor, 22, split with Conor, 18, in the fall due to their schedules.
Song: Some people believe “Everything Has Changed” is about him. She also penned “Starlight” about Ethel Kennedy, Conor’s grandmother.
Taylor just days before their split: “I don’t know how to have a normal relationship because I try to act normal, love from a normal place and live a normal life, but there is sort of an abnormal magnifying glass, like telescope lens, on everything that happens between me and anybody else. I don’t really know that much about love, it turns out.”

NEWS: Taylor Swift's song about her summer with ex Conor Kennedy and his family

Harry Styles (2013): They began dating in November after being spotted holding hands on The X Factor — and even shared a smooch as the clock struck midnight on New Year’s Eve — but as Life & Style exclusively confirmed earlier this week, this duo ended their relationship after only two months of dating.
Song: Following their split, Taylor tweeted "...'til you put me down" — a lyric from her smash hit "I Knew You Were a Trouble" ... but we think Taylor could potentially pen “My Heart Never Went in One Direction” on a future album.
Taylor Talks: But not just yet — though we have a feeling she’ll say something sooner or later!

PHOTO: See Miley Cyrus in bed with Harry Styles post Taylor Swift break up

Which guy did you like Taylor with best? Leave a comment with your answer below!

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