Taylor Swift often references her failed romances in her music – and fans were excited for the release of Speak Now (Taylor’s Version) this week (July 7).
Many fans believed Taylor had found “The One” in Joe Alwyn after they were dating for six years, but they split up earlier in 2023.
Since then, she’s been linked to Matty Healy in an on-off romance, but she’s dated plenty of other famous faces too.
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From the likes of Disney heartthrob Joe Jonas, to Brokeback Mountain star Jake Gyllenhaal, and Twilight hunk Taylor Lautner – the singing sensation has had an impressive back catalogue of romances.
To celebrate the release of Speak Now (Taylor’s Version), Daily Star has a look back at Tay’s past romances.
Joe Jonas
(Image: FilmMagic)
Taylor and Joe dated in 2008 before the Disney heartthrob broke up with her in a reported 25 second phone call. Brutal, right?
But despite the couple having a rocky romance, Taylor allegedly sent him and wife Sophie Turner a gift for their baby.
Things were previously sour for a while though, and Taylor called out the Jonas Brothers’ hunk when she appeared on Saturday Night Live.
In her monologue she famously sung: “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 really well and I’m hosting ‘SNL’ — but I’m not going to write about that in my monologue.”
Taylor Lautner
If they’d have got hitched they’d have been Taylor and Taylor Lautner – so it’s probably safe to say it’s a good thing this romance didn’t last, because the world of showbiz would have been far too confusing.
Taylor Squared – as they were known back in 2009 – met on the set of Valentine’s Day.
Both starring in the rom-com, the pair played boyfriend and girlfriend – something that would soon become real-life for the duo.
The pair broke things off in December 2009, with Taylor reportedly writing Back To December as an apology to the Twilight actor.
At the time of the track coming out Taylor spoke to USA Today where she said: “It’s almost word-for-word.
“It is a song and a conversation that needed to happen because I don’t want to hurt people.
“If you unintentionally do so, you’ve got to make that better.”
John Mayer
(Image: Getty Images North America)
Taylor and John dated for a short while after they worked together on Half Of My Heart, after he reached out to her via Twitter.
Speaking to Elle Magazine about the initial tweet, Taylor said: “I freaked out when I heard, because I’ve been such a big fan of John for such a long time.”
Eyebrows were raised when they dated though, because Taylor was just 19/20, while John was 31/32.
Writing a song about the couple’s relationship after it ended, Taylor wrote Dear John where she addressed her innocence and naivety.
“Dear John, I see it all now, it was wrong.
“Don’t you think 19 is too young to be played by your dark twisted games.”
Speaking to Rolling Stone about the song, John hit back at Taylor when he said: “I will say as a songwriter that I think it’s kind of cheap song writing.”
Jake Gyllenhaal
(Image: Getty Images)
One of the most controversial lovers Taylor has had, Jake Gyllenhall was quite a bit older than Taylor when the pair enjoyed a whirlwind romance.
Inspiring many songs that Taylor has written over the years, the most popular song Jake inspired was All Too Well – plus a few more from her album Red.
Dating for just three months back in 2010, Taylor and Jake were spotted out in the autumn looking loved up on more than one occasion.
She was 20 and he was 29, with it widely reported he broke up with her over text claiming the age gap to be why.
Conor Kennedy
Taylor could have been a Kennedy. Yes, really.
For a short while in 2012 she dated Conor, the grandson of Robert F. Kennedy – who was 18 at the time, while she was 22.
They even spent a romantic weekend together at the exclusive Kennedy compound in Hyannis Port, Mass.
A fan of the Kennedy family before meeting Conor and falling in love, she even wrote a song about his grandfather Robert and his wife Ethel.
The song explores the couple’s relationship when they dated, and is called Starlight. The track features on Taylor’s album Red.
Harry Styles
(Image: GC Images)
Like so many girls, Taylor was a bit of a Directioner too back in the day.
Stepping out with One Direction heartthrob Harry Styles, Taylor left fans divided by the romance.
It all started in December 2012 when the pair were seen on a walk in Central Park.
Their romance only lasted for three months though and ended at the beginning of 2013, and ever since speculation has spiralled over what songs are about the other.
Calvin Harris
(Image: BuzzFoto via Getty Images)
Taylor and Calvin shared a long relationship before things turned slightly sour.
Their relationship began in the beginning of 2015, with the pair going public in the spring and holding hands in public by May.
They then spent July 4 together and then battled break up rumours months after in the autumn, before spending Christmas together.
In March 2016 they celebrated their first anniversary, and one month later Calvin released This Is What You Came For with Rihanna.
The song was written alongside Nils Sjöberg, a name that nobody knew of prior to this banger of a summer tune coming out.
But after Hiddleswift (see below) were seen dancing together at an event Calvin and Taylor split in June.
Tom Hiddleston
(Image: MDM)
Tom Hiddleston and Taylor were first linked when they were seen dancing to a Jay-Z track at the Met Gala in May – when she was still dating Calvin.
Around the same time that Taylor and Calvin split, she was seen stepping out with Tom, and by the end of June 2016 it was reported that Tom had even met her parents.
July 4 – American Independence Day – was when things really hotted up for the pair though.
Staying at Taylor’s Rhode Island home with the likes of Blake Lively and Ryan Reynolds, Tom even wore a vest t-shirt that read: “I [heart] T.S.”
Something she later referenced in the music video for Look What You Made Me Do.
The pair were going strong for a few weeks, before things fizzled out and the pair parted ways.
Joe Alwyn
(Image: WP Pix / SplashNews.com)
Ahhh, good ‘ole Joe Alwyn.
The British-born actor was the guy who seemed to turn Taylor’s hopeless romantic tendencies into the real deal.
Getting together in October 2016 after they met at the Met Gala in September, the pair were going strong for six years.
Thanks to Joe, Swifties were blessed with some real hits from the Reputation album, the loved-up tracks on the Lover album, and the whimsy vibe of Folklore and Evermore – with Joe even co-penning some tracks under the name William Bowery.
At the end of June (2022), rumours began to swirl that the couple had become engaged – “secretly” – however they eventually split up in April of 2023.
Matty Healy
Not long after Taylor split up with Joe, it was reported that she was dating Brit rocker Matty Healy, of The 1975.
They were pictured together in May before reportedly splitting just a month later, however more recent reports suggest they are giving things another go.
A source told The Sun: “There is just something electric between them and they seem to have overcome it all quite quickly and decided they definitely want to make it work at all costs.”
Source: Celebrities - dailystar.co.uk
