Taylor Swift’s Dating History – A Complete List of Boyfriends

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.

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If it isn’t a member of One Direction, then it’s a Hollywood actor. If it isn’t a Twilight heartthrob who captures Tay’s heart, then it’s a world famous DJ. The Evermore 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 dating history…

Ex: Joe Jonas

Who is He? Singer
Dated In: July – Oct 2008

Taylor dated her first famous fella back in 2008, so Joe Jonas can proudly call himself Taylor’s first famous love. The popstars were an item for three 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”.

Ex: Taylor Lautner

Who is He? Actor
Dated In: Aug – Nov 2009

“The Taylors” were the talk 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 Reputation singer and Twilight star apparently had “no chemistry”.

Ex: John Mayer

Who is He? Singer
Dated In: Nov – Feb 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!

Rumored Ex: Cory Monteith

Who is He? Actor
Dated In: 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 rumored that her single, Mine was dedicated to Cory – a guy she dreamed about dating.

Ex: Jake Gyllenhaal

Who is He? Actor
Dated In: Oct – Dec 2010 & Jan – Feb 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.

Fun fact? We Are Never Ever Getting Back Together was in fact based on Taylor’s short-lived romance with Jake!

Rumored Ex: Eddie Redmayne

Who is He? Actor
Dated In: Oct 2011 – Jan 2012

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

Rumored Ex: Zac Efron

Who is He? Actor
Dated In: Feb 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 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?!

Ex: Conor Kennedy  

Who is He? Robert F. Kennedy’s grandson
Dated In: July – Sep 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 two months. Conor, who was 18 at the time, was apparently scared off because Taylor 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.” Even Taylor’s popular music video for Blank Space strongly suggests that it’s based on her past relationship with Conor.

Ex: Harry Styles

Who is He? Singer
Dated In: Dec 2012 – Jan 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.

Harry Styles’ Full Dating History

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.

Ex: Calvin Harris

Who is He? DJ
Dated In: 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.

The duo had such a publicized relationship that they were even 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” during one of her famous feuds.

Ex: Tom Hiddleston

Who is He? Actor
Dated In: June 2016 – Sep 2016

Not long after she split up with Calvin Harris, Taylor bagged herself yet another hot man of the century – and let’s just say she wasn’t low key about it (Marvel fans, if you know, you know).

Fueling romance rumors, she was photographed snogging actor, Tom Hiddleston on a beach in 2016, and for the next few months, the superstars went public with their relationship. The duo split after three months of dating, though, because Tom apparently “grew tired of her”. OUCH!

Boyfriend: Joe Alwyn

Who is He? Actor
Dated In: 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 has starred in movies such as Billy Lynn’s Long Halftime Walk and Keepers. 

This is officially Taylor’s longest relationship and possibly, her most significant yet – and we couldn’t be prouder. Taylor and Joe have been together for four years and perhaps what’s kept their relationship so strong is their privacy. Despite keeping her man low-key however, Taylor has admitted that several songs on her album Folklore are about Joe.

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

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

Which man in her relationship history is Taylor most suited to? Sound off in the comments!



Tale Teller
Angela Stephanou

Angela Stephanou

Owner and chief editor of Tell Tales. Angela has a BA in Communications and oversees the content and strategy across Tell Tales, building an audience of pop culture junkies like herself. Her social media follows have more celebrities than real-life friends, music runs through her veins and she’d much rather be glued to her TV screen, piled under an array of snacks than go out on a Friday night. Angela’s guilty pleasure is watching cheesy reality shows like Keeping Up with the Kardashians, but she’s also a sucker for all things Marvel and DC - two entirely different worlds, we know.

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