Taylor Swift's dating history: who has the singer been linked to?

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Photo credit: Dimitrios Kambouris - Getty Images
Photo credit: Dimitrios Kambouris - Getty Images

Taylor Swift has been an absolute machine when it comes to music releases as of late. She dropped two whole albums during lockdown, Folklore and Evermore, and her latest 'Taylor's version' re-release of Red has got us all discussing her past relationships (as well as who each song could possibly be about).

So, if you're in the business of lyric-deciphering, let's take a trip down memory lane and recap everyone Taylor has dated so far - plus, which songs they *may* have inspired.

Brandon Borello - high school

Taylor reportedly dated Brandon Borello while in high school, though he's managed to remain pretty under the radar. Some of Taylor's OG hits - 'Our Song' and 'Fifteen' - are thought to be about Brandon, which makes sense given the fact that 'Fifteen' tells the story of a high school relationship, while 'Our Song' details the very specific teenage experience of sneaking out to see your SO. The joys of young love, right?

Drew Hardwick - high school

Drew is thought to be another one of Taylor's high school boyfriends, and he gets a special mention in 2007 hit 'Teardrops on my Guitar' when Taylor sings, "Drew looks at me, I fake a smile so he won’t see". Yep, so no disguising that lyric, then.

Joe Jonas - July to October 2008

Photo credit: Jeff Kravitz - Getty Images
Photo credit: Jeff Kravitz - Getty Images

Joe Jonas was Taylor's first high-profile celeb relationship. Despite only dating for around four months, the pair still managed to have a pretty public breakup, with Taylor confirming that he ended things over the phone.

She told Ellen Degeneres in November of the same year: "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."

Taylor later referenced the split again during her 2009 Saturday Night Live monologue, singing, "You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing real well and I’m hosting SNL—but I’m not going to write about that in my monologue."

'Forever and Always' is famously thought to be about Joe, and it's still a banger today.

Lucas Till - March to April 2009

You might recognise Lucas from Taylor's iconic music video for 'You Belong With Me'. While the song isn't actually about him, the pair did date very briefly in 2009.

Later that year, Lucas spoke out about the relationship, telling MTV: "We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other." Shedding light on why they split, he added, "I really just liked her as a friend. That’s the only reason that didn’t work out."

Taylor Lautner - 2009

Photo credit: Jean Baptiste Lacroix - Getty Images
Photo credit: Jean Baptiste Lacroix - Getty Images

Throwback to Taylor Squared, anyone? Following Lucas Till, Taylor went on to date Twilight star Taylor Lautner after meeting on the set of film Valentine's Day where they played a very cringe teenage couple.

They're thought to have broken up around December 2009, with T-Swift releasing 'Back to December' the following year which fans reckon is about Lautner. Asked about the song six years later in 2016, Lautner simply said, "That’s what she does," according to TIME. Ouch.

John Mayer - December 2009 to February 2010

Photo credit: Dimitrios Kambouris - Getty Images
Photo credit: Dimitrios Kambouris - Getty Images

Who could forget John Mayer? Taylor and John dated briefly between 2009 and 2010, with the relationship leading to the iconic song 'Dear John'. Lyrics include, "Dear John, I see it all now I was wrong. Don’t you think 19 is too young to be played by your dark, twisted games?" and the whole thing was a huge burn.

John didn't take the single lightly though, telling 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." He also criticised Taylor's writing, adding, "I will say as a songwriter that I think it’s kind of cheap songwriting."

Jake Gyllenhaal - October 2010 to January 2011

Photo credit: Robert Smith - Getty Images
Photo credit: Robert Smith - Getty Images

Ah, Jake Gyllenhaal. Anyone not living under a rock will know the majority of songs on Taylor's 2012 album Red are thought to be about Jake - thanks to its recent resurgence in the re-released Red (Taylor's version).

Of course, the single we're all talking about is 'All Too Well', with the 2021 All Too Well: The Short Film supposedly telling the story of Jake and Taylor's age gap relationship (Jake was 29 and Taylor was 20 when they dated).

The real question though: did Taylor ever get her scarf back?

Connor Kennedy - July to October 2012

Taylor and Connor, a member of the famous US Kennedy family, were first reported to be dating after being pictured together in Massachusetts in 2012. They called time on their romance after just a few months, though the split is thought to have been amicable.

Harry Styles - November 2012 to January 2013

Photo credit: David Krieger/Bauer-Griffin - Getty Images
Photo credit: David Krieger/Bauer-Griffin - Getty Images

These two very famously dated for a brief but drama-filled few months. They were first pictured together on an autumn walk around Central Park, followed by a (slightly cringe) New Year's kiss in Times Square. The pair later split, with the songs 'Out of the Woods' and 'Style' thought to be very obviously about Harry.

Calvin Harris - February 2015 to May 2016

Photo credit: Larry Busacca/BMA2015 - Getty Images
Photo credit: Larry Busacca/BMA2015 - Getty Images

Calvin and Taylor were pretty wholesome vibes for a while, pictured out and about in matching outfits and sharing some cute PDA at the 2016 Billboard Awards.

Plus, there's even a picture of the moment they met in 2015, and we're obsessed.

However, things didn't stay rosy for long. The pair split in May 2016, with Calvin even supposedly referencing Taylor in some cryptic song lyrics.

Tom Hiddleston - May to September 2016

Photo credit: starzfly/Bauer-Griffin - Getty Images
Photo credit: starzfly/Bauer-Griffin - Getty Images

News of Taylor and Tom's relationship first broke when they were pictured kissing in some very unexpected PDA.

Things seemed to get serious from there, with Tom famously pictured wearing an 'I HEART TS' vest during the couple's 4th July beach trip with a long list of famous friends.

Well, that's one way to show you're committed. Sadly, it didn't last, with the pair splitting after around four months.

Joe Alwyn - May 2017 to present

Photo credit: Jackson Lee - Getty Images
Photo credit: Jackson Lee - Getty Images

Taylor and current boyfriend Joe Alwyn have been going strong for over four years now, though they've managed to keep their relationship pretty under wraps.

Many of Taylor's love songs from her past four albums - including Reputation, Lover, Folklore and Evermore - are thought to be about Joe. She's since spent plenty of time with Joe in his native London - with Lover album track 'London Boy' telling you everything you need to know.

As of the end of 2021, these two are still as cute as ever and, yep, we're obsessed.

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