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

Remember Taylor's fling with Harry Styles? What a time to be alive...
BY
Taylor Swift's dating history

Last modified December 12th 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.

RELATED:
40 Cool Taylor Swift Facts You Didn’t Know

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 in a suit
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 selfie
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 swift with taylor lautner and his wife
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 playing the guitar
johnmayer | Instagram

SEE ALSO:
Katy Perry’s Dating History – List of Boyfriends


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 doing the peace sign
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.

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. The popular stars triggered romance rumors when they were spotted hand-in-hand at Central Park Zoo and kissing on New Years Eve, but the whole thing came crashing down way too soon.

CHECK OUT:
Harry Styles’ Full Dating History

The very-much publicized relationship came to an end after just one 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.

Rumored Ex: Matt Healy

Who is He? Singer
Dated In:
December 2014 (dated again in 2023 – scroll down!)

There’s absolutely no confirmation that Taylor and The 1975’s Matt Healy dated in 2014, but there is *some* evidence that suggested so. After being spotted at his concerts, Matt admitted to “exchanging numbers” with Tay: “We exchanged numbers. Let’s see what happens. I mean bloody hell, what am I going to do? Go out with Taylor Swift? She’s a sensation, I wouldn’t say no.”

Update: Taylor and Matt rekindled their romance in 2023, but broke up again soon after – scroll down for more deets!

Matt Healy
itslilynelson | Instagram

Ex: Calvin Harris

Who is He? DJ
Dated In: March 2015 – June 2016

After more than one year of (officially) staying single, Taylor found herself another famous boyfriend. She dated DJ, Calvin Harris from March 2015 until June 2016.

From wearing matching outfits to posting anniversary messages, 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. Considered one of Taylor’s biggest controversies, it was also believed that Taylor cheated on him with Tom Hiddleston. The truth is, “it was the wrong situation. It clearly wasn’t right, so it ended,” Calvin later told GQ.

taylor swift hugging calvin harris
taylorswift | Instagram

Ex: Tom Hiddleston

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

Just two weeks 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 Marvel actor, Tom Hiddleston on a beach in 2016, and for the next few months, the superstars went public with their relationship. From dancing at a Selena Gomez concert, to wearing an “I love T.S.” shirt, Taylor and Tom were clearly having fun together.

The pair split after three months of dating, though, because Tom “wanted the relationship to be more public than she was comfortable with.”

Ex: Joe Alwyn

Who is He? Actor
Dated In: May 2017 – April 2023

Taylor sure has a thing for British men! The most recent in her dating history and long line-up of boyfriends is actor, Joe Alwyn, who has starred in movies such as Billy Lynn’s Long Halftime Walk and Keepers. 

After staying together for six years, this was officially Taylor’s longest relationship and most significant yet – marriage was even on the cards!

Taylor and Joe may have broken up due to the relationship “running its course”, but perhaps what kept their relationship so strong was their privacy. Despite keeping her man low-key during the romance, however, Taylor has admitted that several songs on her album Folklore were about Joe.

Ex: Matt Healy

Who is He? Singer
Dated In: May – July 2023

If there was any proof that Taylor Swift and Matt Healy were dating again, it’s this photo.

Indeed, the Eras hitmaker and 1975 star were spotted holding hands and reportedly “kissing” on a private NYC date back in May. These photos came soon after the pair sparked romance rumors earlier in the month when Matt was spotted at one of Taylor’s concerts and they were photographed leaving together.

Sources at the time claimed, “It’s super-early days, but it feels right…[they’re] madly in love.”

But just two months later, it was reported that Taylor and Matt had broken up. “They are absolutely not together and aren’t even in contact anymore. She is enjoying being single and has been spending time in the studio and hanging out with friends…,” People asserted.

Boyfriend: Travis Kelce

Who is He? American footballer
Dated In: Sep 2023 – now

Just a few months after the Matt Healy fiasco, Taylor is back in the dating game!

In September 2023, rumors were rife that Taylor was hooking up with Kansas City Chiefs tight end, Travis Kelce, after photos of the singer were captured at his game. Tay and Travis were also photographed leaving the game together, heading their way to what was apparently an “intimate dinner.”

The pair were soon spotted hand-in-hand, pretty much confirming that they are indeed, a real couple. And it wasn’t long before Taylor revealed to TIME Magazine that she’s been dating Travis long before she was spotted at his game:

“We actually had a significant amount of time that no one knew, which I’m grateful for, because we got to get to know each other. By the time I went to that first game, we were a couple…”

taylor swift kissing travis Kelce
patty_cuts | Instagram

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? 

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

Share
Tweet
Pin
Share
Share
Email

Tale Teller

  • Angela Stephanou

    After completing her BA in Communication, Media and Film studies, Angela launched Tell Tales Online, and now writes and oversees the content and strategy across the site. As a pop culture junkie, she follows more celebs than real-life people, her guilty pleasure is watching The Kardashians, but she's also a fan of Marvel and Game of Thrones.

Subscribe
Notify of

0 Comments
Inline Feedbacks
View all comments