Who Are Taylor Swift's Ex-Boyfriends? An Extensive List Of All The Men She's Loved Before

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Who Are Taylor Swift's Ex-Boyfriends? An Extensive List Of All The Men She's Loved Before
Entertainment And News

When you think of Taylor Swift, you might think of a pop star who has dominated the charts since the end of the aughts. You might think of a singer-songwriter who made the jump from country to pop without even messing up her hair. You might even think of her Instagram, filled with her cats and her girl squad.

She just took home six American Music Awards, including the award for favorite pop/rock artist, favorite adult contemporary artist, and artist of the year! But when we really think about her, it's her dating life that comes to mind.

Who are Taylor Swift's ex boyfriends? 

Her romantic past has been an object of fascination to her fans and the world at large almost since she first burst onto the scene. Though she's happily in a long-term relationship, taking a walk through her past relationships makes it easy to see where she gets the inspiration for all of those songs. 

RELATED: Five Super-Weird Things You Never Knew About Taylor Swift's Boyfriend Joe Alwyn

1. Her current beau, Joe Alwyn

People like to talk a big game about how Swift is always dating some new guy, but let the record show that she and actor Joe Alwyn have been together since May 2017. That's as long as I've been with my boyfriend and I'm no Taylor Swift. 

The singer knew she would be under a microscope dating someone new, so she made triple sure to keep what they had on the down-low until they were officially official. Taylor wasn't above getting a little theatrical about it all either. In fact, to throw off the press during the early days of their courtship, she went so far as to wear stuff like wigs and other disguises to meet Alwyn privately. 

Like the men who came before, many believe he inspired Taylor. In particular, they believe the songs "Ready For It," "Gorgeous," and "King of My Heart" are all about Alwyn. There's even rumors they're engaged.

2. Calvin Harris & Tom Hiddleston

Ah, the gilded and drama-filled years before she got serious with Joe! I have to admit, I kind of yearn for them. Remember all of the speculation that went on when she was enjoying relationships with DJ Calvin Harris and actor Tom Hiddleston?

Swift met Harris in 2015, and while things started off nice and casual, they soon got serious. Folks believe she wrote "Look What You Made Me Do" for the guy. “For the first time, I had the most amazing person to come home to when the spotlight went out and when the crowds were all gone,” she said about Calvin while making an award acceptance speech. 

But then, just months later, she was spotted out on the town with Tom Hiddleston before even announcing their split. Ultimately, that led to the DJ dropping his own message about the end of the relationship on Twitter, one she "Swiftly" (I'm so sorry) shared herself. 

“The only truth is that a relationship came to an end & what remains is a huge amount of love and respect,” he tweeted at the time. Swift retweeted the message and then dropped Hiddleston almost as quickly as she picked him up, making fans speculate that it was just for attention.

RELATED: What Really Went Down In The Taylor Swift/ Karlie Kloss Feud — And Why It's Far From Over

3. Jake Gyllenhaal

Earlier in her career, like, late 2010, Swift embarked on a short tryst with Jake Gyllenhaal. People couldn't handle it. Everyone was all delighted that Taylor was going to finally settle down, but she was only 20 years old at the time Gyllenhaal was almost a decade older.

Age is just a number, sure, but there's a lot of life experience that happens between 20 and 30. Eventually, after about three months, they broke up. 

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There was a lot of speculation about why they broke up and about who pulled the trigger, particularly after she released the song "We Are Never Getting Back Together," which many believed to be a dig at Jake. Ultimately, the obvious answer is also sometimes the right one: they weren't the perfect match and she wasn't ready to get serious with him. 

4. Harry Styles

Taylor Swift's dating life hit peak fan girl in November 2012 when she started dating Harry Styles. Fans were first tipped off when Swift began wearing a silver airplane necklace that matched Harry's. Their winter romance was, pardon the pun, swift.

They were photographed together on a date in Central Park in December. Sometime that month, the couple was in a snowmobile accident that resulted in a trip to the hospital and 20 stitches.

Over the holidays, Haylor went to the British Virgin Islands together and were done soon after they returned, allegedly because they were both busy and never in one place for long. She also allegedly wrote the song "Out of the Woods" about her relationship with Styles.

5. John Mayer

Do you know how in fairy tales the protagonist will arrive at a bridge that they need to cross, only in order to cross said bridge they have to pay a toll to some vicious troll? I think of that every time I hear of another starlet embarking on a relationship with John Mayer.

After Jake, that's exactly what Taylor did, and it didn't last, obviously, but hey, at least we got "Dear John" out of it. And did you think you were going to escape this part of Swift's past love life without hearing how John Mayer felt about it? Heck no.

“It made me feel terrible. Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do,” he said in an interview. It should be noted that Mayer is 12 years older than Swift and sounds ridiculous lecturing her on her maturity level. At least he didn't call Taylor sexual napalm.  

6. Joe Jonas & Taylor Lautner 

To take you even further back, in 2008 for another three month period, Swift dated Joe Jonas. They were cute but unremarkable in the face of the magic that was about to blow everyone away: Taylor and Taylor. That's right, while filming the movie Valentine's Day, Swift met Taylor Lautner and pretty soon the duo was completely inseparable.

But that relationship wasn't exactly long-lived either. In fact, this is a relationship that Swift takes full responsibility for crumbling ahead of its time in the form of the song "Back to December." While talking about it, she really opened up: “It was about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him. So this is a song full of words that I would say to him, that he deserves to hear,” Swift said.

RELATED: Scott Borchetta Can't Seem To Stop Mansplaining The Big Machine Sale To Taylor Swift

Rebecca Jane Stokes is a humor and lifestyle writer living in Brooklyn, New York with her cat, Batman. For more of her work, check out her Tumblr.

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Editor's Note: This article was originally posted on November 25, 2019 and was updated with the latest information.