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A look back at Taylor Swift’s star-studded dating history

Earlier this week it was reported that Taylor Swift is dating The 1975 frontman Matty Healy.

The news came after the singer’s recent split from Conversations with Friends actor Joe Alwyn.

We’ve taken a look back over Taylor’s dating history.

Here’s a complete timeline:

Joe Jonas

Taylor dated Joe Jonas between July and October 2008.

That November, the singer released a track titled Forever & Always about her ex.

The singer confirmed that the Jonas Brothers star had ended things with her over the phone, telling Ellen DeGeneres: “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.”

The pair are now on good terms, with Joe and his now-wife Sophie Turner openly supporting Taylor’s ventures.

Lucas Till

Taylor is said to have briefly dated Lucas Till in 2009.

The actor appeared in the blonde beauty’s music video for You Belong With Me.

He previously told MTV of their romance: “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.”

Taylor Lautner

Taylor dated Taylor Lautner at the end of 2009.

The pair met on set of rom-com Valentine’s Day (2010), in which they played a loved-up on-screen couple.

The Twilight actor presenter his then-girlfriend with the MTV VMA for best female video for You Belong With Me.

However, the sweet moment turned notoriously sour when Kanye West stormed up on stage stating: “Yo, Taylor, I’m really happy for you, Imma let you finish, but Beyoncé had one of the best videos of all time!”

John Mayer

Taylor dated John Mayer for a couple of months between December 2009 and February 2010.

The former couple’s breakup made headlines when John reacted badly to Taylor’s track Dear John, which was inspired by him.

At the time, he told Rolling Stone: “I never got an email. I never got a phone call. I was really caught off guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if at the lowest you’ve ever been, someone kicked you even lower?”

“I will say as a songwriter that I think it’s kind of cheap songwriting. I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bulls**t.”

Jake Gyllenhaal

Taylor dated Jake Gyllenhaal between October 2010 and January 2011.

A source told Us Weekly at the time of their split: “It was a 180-degree turn and so out of the blue. Jake just told her it wasn’t working out… Taylor is really upset and hurt. She doesn’t know what she did for him to put a stop to it. She feels really burned by him.”

The singer’s iconic song All Too Well is inspired by her relationship with the actor.

In the song, Taylor points out their 11-year age gap as she sings about their breakup, sining: “They say all’s well that ends well, but I’m in a new hell every time you double-cross my mind. You said if we had been closer in age maybe it would have been fine, and that made me want to die.”

The lyrics continue: “The idea you had of me, who was she? A never needing ever lovely jewel whose shine reflects on you, not weeping in a party bathroom. Some actress asking me what happened, you, that’s what happened, you.”

The new 10-minute version of All Too Well referenced a story told on another song from Taylor’s album Red called The Moment I Knew, where Jake disappointed her by skipping her 21st birthday party.

Taylor sings: “You, who charmed my dad with self-effacing jokes, sipping coffee like you were on a late night night show. But then he watched me watch the front door, all night, willing you to come, and he said, ‘It’s supposed to be fun, turning 21.’”

Months after being slammed by Swifties for breaking their idol’s heart, Jake broke his silence on the song, telling Esquire: “It has nothing to do with me. It’s about her relationship with her fans. It is her expression.”

“Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”

When asked specifically if he’s listened to Red (Taylor’s Version), Jake replied: “No.”

Connor Kennedy

Taylor dated Connor Kennedy between July and October 2012.

Us Weekly broke the news of their romance after they were papped together in Hyannisport, Massachusetts.

According to E! News, the pair’s split was “totally amicable and down to the distance between them”.

Harry Styles

Taylor and Harry Styles dated between November 2012 and January 2013.

Taylor has written two songs about her relationship with Harry – Style and Out of the Woods’; while Swifties also believe that I Knew You Were Trouble is also about the former boyband member.

It is believed that One Direction’s song Perfect’, which Harry co-wrote, is about Taylor.

The former couple recently proved there is no bad blood between them, as they reunited at the 2023 Grammy Awards back in February.

Calvin Harris

Taylor met Calvin Harris at the Elle Style Awards in February 2015.

The following months they were spotted wearing matching outfits at a Whole Foods in Nashville, Tennesse, and went public with their relationship at the Billboard Music Awards that May.

The former couple celebrated their one-year anniversary on March 6, 2016, but just two months later they parted ways.

Swifties theorise that Taylor’s track I Forgot You Existed from her Lover (2019) album was written about Calvin.

Tom Hiddleston

Taylor dated Tom Hiddleston between May and September 2016.

The pair first sparked romance rumours at the Met Gala, and the following month they were papped kissing in Rhode Island.

During their brief romance the actor, who plays Loki in the Marvel Cinematic Universe, met his girlfriend’s parents, accompanied her to her best friend Selena Gomez’s concert, and was even spotted sporting an “I HEART TS” top.

Taylor’s tracks Getaway Car, Cruel Summer, I Did Something Bad, Midnight Rain, Long Story Short and evermore are said to be inspired by her romance with Tom.

Joe Alwyn

Taylor is rumoured to have met Joe Alwyn at the Met Gala back in 2016.

One year later The Sun broke the news that the couple were dating, saying she’d been staying in London in disguise.

Last July there was speculation that the couple had been engaged for a number of months; however, these rumours were never confirmed.

Earlier this year, it was reported that Taylor and Joe had split after six years together.

Matty Healy

Earlier this week it was reported that newly-single Taylor is “madly in love” with The 1975 frontman Matty Healy.

According to The Sun, the pair recently struck up a romance, almost ten years after they briefly dated back in 2014.

A source close to Taylor told the publication: “She and Matty are madly in love. It’s super-early days, but it feels right. They first dated, very briefly, almost ten years ago but timings just didn’t work out.”

“Taylor and Joe actually split up back in February, so there was absolutely no crossover.”

 

“Both Matty and Taylor have been touring over the past few weeks, so it’s been a lot of Face-Timing and texting but she cannot wait to see him again,” the source continued to tell the publication.

“But as two international megastars, they understand the pressures of one another’s jobs better than anyone, and are incredibly supportive of their respective careers.”

“They are both massively proud and excited about this relationship and, unlike Taylor’s last one — which was very much kept out of the spotlight, deliberately — she wants to ‘own’ this romance, and not hide it away,” the insider continued.

“Taylor just wants to live her life, and be happy. She’s told pals Matty is flying to Nashville over the weekend to support her on the next leg of her tour.”

Before rekindling their romance, Taylor made a surprise appearance at The 1975’s gig at London’s O2 Arena back in January – which sent fans into a frenzy.

The source added: “Taylor’s pals are absolutely delighted because they reckon she and Matty are a brilliant match. Obviously putting two such ­famous names together means a lot of fan attention and a LOT of eyeballs on the pair.”

“But Matty and Taylor are sensible enough, and fame-equipped enough, to handle it. Both of them have been — often unfairly — dragged through the ringer on a global scale.”

“But crucially, they’re both brilliant, smart, kind people and, quite simply, have each other’s backs,” they added.

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