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


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Last modified Aug 2nd 2023.

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 Marvel 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 has Taylor dated and which A-list boys has the pop princess been basing her heartbreak songs on? Here’s a timeline of Taylor Swift’s dating history, including all of her exes…

Ex: Joe Jonas

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

Joe Jonas can proudly call himself Taylor’s first love. Taylor dated her first famous fella back in 2008, just before he hooked up with Demi Lovato.

The popstars were an item for three months before the teen idol broke up with her during a 27-second phone call.

“When I find that person who is right for me, he’ll be wonderful, and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she told Ellen DeGeneres.

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”.

joe jonas
joejonas | Instagram

Ex: Lucas Till

Who is He? Actor
Dated In: March – April 2009

After meeting on the set of her You Belong With Me music video, Taylor and actor Lucas Till began dating. It was a short-lived romance, however, as the fling only lasted around one month.

Lucas told MTV, We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other…[but] most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”

lucas till
lucastill | Instagram

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 as a couple for three months. Despite sharing the same name, the Reputation singer and Twilight star apparently had “no chemistry”.

Many years down the line and the two Taylors reunited! Swift joined Lautner for the I Can See You music video and the actor joined Swift on stage during her Eras Tour show.

taylor lautner taylor swift
taylautner | Instagram

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!

john mayer
johnmayer | Instagram

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.

They were also photographed together on numerous occasions – at a bowling alley and a late night dinner.

cory monteith
gleeofficial | Instagram

Ex: Jake Gyllenhaal

Who is He? Actor
Dated In: Oct 2010 – Jan 2011

From one famous guy, to the next! Taylor was romantically involved with Hollywood actor, Jake Gyllenhaal for three months in 2010-2011.

According to Us Weekly, the highly-publicized 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 just 21.

After Jake surprisingly told Taylor it wasn’t working out, the singer was completely heartbroken over the split, so much so, that she based her heartbreak songs, We Are Never Ever Getting Back Together and All Too Well, on him.

Rumored Ex: Chord Overstreet

Who is He? Actor
Dated In: February 2011

There’s not much to this so-called relationship, but since they were seen on a date together, Chord Overstreet definitely has a place in Taylor Swift’s dating history!

Taylor and Glee‘s Chord Overstreet were spotted hanging together at an L.A. Kings NHL home game, with a source claiming, “after the event, Taylor and Chord grabbed a bite. He’s into her.”

chord overstreet
chordoverstreet | Instagram

Rumored Ex: Eddie Redmayne

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

Add a UK hottie to Taylor’s love-list! She allegedly had a three-month fling with Fantastic Beasts actor, Eddie Redmayne from 2011 to 2012.

Apparently, Eddie didn’t want a long-distance relationship. 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?!

zac efron
zacefron | Instagram

Ex: Conor Kennedy  

Who is He? Robert F. Kennedy Jr.’s son
Dated In: July – Sep 2012

Another man who made it in Taylor’s life was Robert F. Kennedy Jr.’s son, Conor Kennedy. The two lovebirds had a small summer romance that barely lasted two months, which involved a lot of PDA around the Kennedy compound in Massachusetts.

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.