A Timeline of Taylor Swift’s Boyfriends – From Harry Styles to Calvin Harris

Taylor Swifts boyfriends

Taylor Swift has had her fair share of men, hasn’t she? They’re not just any kind of men from backstage or from her squad; these lucky guys are almost always of the famous kind. If it isn’t a member of One Direction, then it’s a Hollywood actor. If it isn’t a Twilight heartthrob who captures TayTay’s heart then it’s a world famous DJ. The Folklore singer really does get her hands on the hottest of celebrity men. 

So who are these A-list boys that the pop princess has been basing her heartbreak songs on? Here’s a timeline of Taylor Swift’s boyfriends…

Joe Jonas: July – October 2008

Taylor dated her first famous fella back in 2008. Joe Jonas can proudly call himself Taylor’s first famous love. The two popstars were an item for 3 months before the teen idol broke up with her during a 27-second phone call. At first, Joe was accused of cheating on Taylor but he confirmed that this wasn’t the case in a heartfelt letter to fans. He said that his “heart moved on” and his “feelings changed”.

taylor swift joe jonas


Taylor Lautner: August – November 2009

“The Taylors” were on everyone’s lips in 2009! Swift and Lautner took their high-school romance from the movie, Valentine’s Day off-screen and lasted for three months. Despite sharing the same name. the singer and Twilight star apparently had “no chemistry”.

taylor swift and taylor lautner

New Line Cinema

John Mayer: November – February 2010

Taylor was linked to a much older, famous guy – John Mayer for a short period of time however things ended rather bitterly. As per usual, Taylor decided to write a song about her ex (Dear John) which left him a little pissed off. John told Rolling Stone “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.” Let’s not forget that Taylor’s relationship with John also triggered her never-ending feud with Katy Perry!

taylor swift john mayer


Cory Monteith: April – May 2010

Although it was never confirmed, Taylor apparently had a small spark with Glee’s late star, Cory Monteith in 2010. The two never admitted to dating each other but it was rumoured that her single, Mine was dedicated to Cory – a guy she dreamed about dating.

taylor swift and cory monteith


Jake Gyllenhaal: October – December 2010 and January – February 2011

From one famous guy, to the next! Taylor was romantically involved with Hollywood actor, Jake Gyllenhaal in both 2010 and 2011. According to US Weekly, the on-and-off relationship ended because Jake hated the camera attention and could “feel the age difference” between them. He was 29 at the time while Taylor was 21. We Are Never Ever Getting Back Together was in fact based on Taylor’s short-lived romance with Jake!

taylor swift Jake Gyllenhaal


Eddie Redmayne: October 2011 – January 2012

Add a UK hottie to Taylor’s lovelist! She allegedly had a 3-month fling with The Theory of Everything actor, Eddie Redmayne from 2011 to 2012. To this day, the Oscar-winner denies ever dating Taylor but reports back then claim the two met and fell for each other when she was about to be casted alongside him in Les Misérables.

taylor swift eddie redmayne

Zac Efron: February 2012 – March 2012

Taylor and Zac Efron may not have made their relationship official, but that didn’t stop the dating rumors from swirling. Fans suspected a romance when the two were promoting their movie, The Lorax however they shut down rumors on Ellen DeGeneres’ show. They both set the record straight and confirmed that they were never a couple by singing a parody song together. But still, who’s to say sparks didn’t fly between them?!

taylor swift and zac efron

The Ellen DeGeneres Show

Conor Kennedy: July – September 2012  

Another man who made it in Taylor’s life was Robert F. Kennedy’s son, Conor Kennedy. The two lovebirds had a small summer romance that lasted barely 2 months. Conor, who was 18 at the time was apparently scared off because Taylor, 22 came on too strong. According to RadarOnline, the singer was allegedly “obsessed with the idea of dating a Kennedy, than the actual Kennedy she was dating.” Her music video for Blank Space strongly suggests that it’s based on her past relationship with Conor!

taylor swift Conor Kennedy


Harry Styles: December 2012 – January 2013

Taylor Swift’s ex boyfriends really are what dreams are made of! Taylor had Directioners green with envy back in 2012 when she dated Harry Styles. The very-much publicized relationship came to an end after a month causing Taylor to write a whole album (1989) about it. She even hinted at hers and Harry’s romance in her Style music video. We have a feeling her split with Harry broke her heart the most.

Taylor Swift Harry Styles


Calvin Harris: March 2015 – June 2016

After one whole year of surprisingly staying single, Taylor found herself another famous boyfriend. She dated DJ, Calvin Harris from March 2015 until June 2016 .Calvin was so into Taylor that he defended her in arguments and she’d even said the “L” word to him! In fact, the duo had been ranked as the highest-paid celebrity couple with combined earnings of over $146 million! Things turned sour later on though when Calvin accused Taylor of trying to make him ‘look bad’ and ‘bury him like Katy Perry’ in a Twitter rant.

taylor swift calvin harris

taylor swift | Instagram

Tom Hiddleston: June 2016 – September 2016

Not long after she split up from Calvin Harris, Taylor Swift was photographed snogging actor, Tom Hiddleston on a beach! She went and bagged herself yet another hot man of the century, ladies and gents! Taylor could have been a little more “low key” about getting a new boyfriend, though (if you’re a Marvel fan, you’ll get it)! The duo split after 3 months of dating because Tom apparently “grew tired of her”. OUCH!

Joe Alwyn: May 2017 – Present

Taylor sure has a thing for British men! The latest in her long line-up of boyfriends is actor, Joe Alwyn who starred in movies such as Billy Lynn’s Long Halftime Walk and Keepers. The relationship may not be official but the duo have been spotted together a few times now. E! News reports that the couple’s relationship has reached levels of exclusivity, with Taylor introducing Joe to squad members Selena Gomez, Gigi Hadid, and other “close friends.”

We bet you thought this list of Taylor Swift’s boyfriends would never end! Her love life really is an ongoing saga. Taylor’s had more famous former flames than we can count on one hand and she’s not afraid to sing about them in her music.

Bagging hot, rich superstars sure comes easy to her. How many more will Taylor get through? Who will she be penning lyrics about next? Joe Alwyn better keep Taylor sweet!

Want to know more about the superstar? We’ve unwrapped 21 cool Taylor Swift facts we bet you never knew until now!

Tale Teller

As an avid blogger and someone who eats, sleeps and breathes entertainment, I decided to take matters into my own hands and establish a showbiz-themed website. Ever since I can remember, I've been interested in the world of celebrities, have listened to the latest music, and watched the newest movies. My guilty pleasure is watching cheesy reality shows like Keeping Up with the Kardashians, but I’m also a sucker for all things Marvel and DC - two entirely different worlds, I know. Other than writing about showbiz, I’m also a part-time freelancer, crafting articles for websites like Career Addict and Pangea.

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