The famous exes who were almost Mr Swift! Before finding love with actor Joe Alwyn, popstar Taylor racked up a string of high-profile relationships – and breakups – with stars including Tom Hiddleston, Calvin Harris and Harry Styles
- Taylor Swift, 32, is engaged to her British boyfriend, actor Joe Alwyn
- A source claiming to be close to Joe said their inner circle was staying mum
- Singer has been dating actor since 2016 – but has a bumpy relationship history
- Previously was in a relationship with popstars Joe Jonas and Harry Styles
- Also was courted by A-listers Jake Gyllenhaal and Tom Hiddleston
- Most high profile relationship was Calvin Harris, and they had a bitter breakup
Taylor Swift has reportedly been engaged to her boyfriend of more than five years, Joe Alwyn, for a ‘few months.’
The popstar, 32, began dating the Conversations With Friends star, 31, in late 2016 after they were rumored to have crossed paths at that year’s Met Gala in New York City.
And now The Sun claims that the singer has been wearing an engagement ring ‘behind closed doors’ and that the couple have only informed their close friends of the news.
However it hasn’t been an easy road to love for Taylor, who has had multiple high profile relationships – and break ups – in the spotlight, including with her most serious ex-boyfriend, Calvin Harris.
From a fling with Harry Styles to her first boyfriend Joe Jonas, here FEMAIL reveals Taylor’s path to a fairytale ending….
Taylor Swift has reportedly been engaged to her boyfriend of more than five years, Joe Alwyn, for a ‘few months’ – but the road to love hasn’t always been smooth for the singer (pictured, with her ex Calvin Harris)
It hasn’t been an easy road to love for Taylor, who has had multiple high profile relationships – and break ups – in the spotlight, including with exes Jake Gyllenhaal (left) and Harry Styles (right)
Meanwhile the singer enjoyed a very public relationship with actor Tom Hiddleston before meeting Joe
July- October 2008: JOE JONAS
Taylor dated Joe in the early days of her singing career back in 2008, but sadly split after only a few months together.
The singer revealed that she was dumped over ‘phone call’ and their relationship was inspiration for the star’s much-loved album Fearless.
The Grammy-winning songstress then went onto slam Joe during an appearance on The Ellen Show, saying: ‘There’s one (song) that’s about that guy, but that guy’s not in my life anymore, unfortunately. That’s ouch.
‘We haven’t talked since, but you know what, some day I’m gonna find someone really really great who’s right for me.’
Taylor dated Joe in the early days of her singing career back in 2008, but sadly split after only a few months together
‘When I look at that person, I’m not even going to remember the boy who broke up with me over the phone in 25 seconds when I was 18.’
But in 2015, Joe revealed he harboured no bad blood with Taylor during an interview with Access Hollywood, admitting that having a song written about you goes with the territory of dating a musician.
And in 2021, Taylor hinted that she and Jonas were back on civil terms during another appearance on Ellen’s Burning Questions segment.
The star was asked what the most rebellious thing she did as a teenager was, which caused Taylor to laugh.
‘Probably when I like put Joe Jonas on blast on your show,’ she began. ‘That was too much, that was too much.’
Meanwhile last year, Taylor put out previously unreleased track Mr. Perfectly Fine which is believed to be about ex Joe.
The singer revealed that she was dumped over ‘phone call’ and their relationship was inspiration for the star’s much-loved album Fearless
During an appearance on the Ellen Show, Taylor revealed Joe had dumped her over the phone in a brief phonecall
It’s about a guy who broke Taylor’s heart and moved on without issue while she picked up the emotional pieces – very of-the-moment for 2008 Taylor who was still in her teens.
‘Hello, Mr. Perfectly fine / How’s your heart after breaking mine?/ Mr. always at the right place at the right time, baby / Hello, Mr. casually cruel / Mr. everything revolves around you / I’ve been Miss misery since your goodbye / And you’re Mr. perfectly fine,’ Taylor croons.
August – November 2009: TAYLOR LAUTNER
Taylor and Taylor dated back in 2009, having first met while filming the upcoming ensemble romantic comedy Valentine’s Day, where they shared an on-screen kiss.
Taylor and Taylor dated back in 2009, having first met while filming the upcoming ensemble romantic comedy Valentine’s Day, where they shared an on-screen kiss.
She described the moment as ‘life-changing’, and he appeared equally smitten, saying he definitely considered her ‘his type’.
When quizzed about their relationship on a U.S. radio show at the time, the Love Story singer played it coy.
She said: ‘I don’t know, he’s an amazing guy and we’re really close… and ah… yep.’
However it was a mere two months before their relationship was over.
‘He liked her more than she liked him. He went everywhere he could to see her, but she didn’t travel much to see him,’ a source told Us Weekly at the time. ‘They decided they were better as friends.’
It has long been rumoured that Swift wrote Back To December about her 2009 relationship with Lautner.
Many Swifties believe that the track released from the ‘vault’ is indeed about Joe as Taylor previously admitted to writing Fearless song Forever And Always about her relationship with Jonas and that since Mr. Perfectly Fine did not make the cut of the 2008 album it was likely written at the same time.
However Swift has not confirmed whether the track about a long lost love who ‘looked me in the eye and told me you would never go away’ is indeed about The Jonas Brothers member.
Things seem to be all good between the duo as Swift had mentioned in her 2020 song Invisible String that she had sent Joe and his new wife Sophie Turner a present for their baby girl, Willa, who was born last July.
November 2009 – February 2010: JOHN MAYER
John Mayer reportedly dated Taylor from December 2009 through February 2010 when he was 31 and she was 19.
They originally met when she collaborated on his song Half of My Heart.
The romance seemingly ended on bad terms based on her scathing song Dear John which many people believe is about him.
The name of the song as well as lyrics recalling her age (19) at the time of the romance appear to lead to the conclusion that is is fact about John and their rocky but brief romance, although the songstress never confirmed it was about him.
The timing of the song also confirms its about John: She released the song in October 2010 on her Speak Now album, eight months after their reported split.
The tune gave insight on how Taylor and John’s reported romance went wrong, with the singer singing in tune: ‘Dear John, I see it all now that you’re gone/ Don’t you think I was too young to be messed with / The girl in the dress cried the whole way home.’
She also wrote the lyrics: ‘Well maybe it’s me / And my blind optimism to blame / Or maybe it’s you and your sick need / To give love and take it away.
‘Dear John, I see it all now, it was wrong / Don’t you think nineteen’s too young / To be played by your dark, twisted games.’
He added more fuel to the fire two years after the songs release when he told Rolling Stone magazine that he felt ‘really humiliated’ about the song, which ‘made’ him ‘feel terrible.’
He said to the outlet in the 2012 interview: ‘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.’
He said at the time that he didn’t know how she felt until after the song was released: ‘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?’
He also took a swipe at Taylor’s songwriting in the candid interview: ‘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 bull***t.’
John Mayer reportedly dated Taylor from December 2009 through February 2010 when he was 31 and she was 19
The romance seemingly ended on bad terms based on her scathing song Dear John which many people believe is about him
After his pointed words, Taylor was asked her thoughts about what he told Rolling Stone.
She told Glamour magazine: ‘How presumptuous! I never disclose who my songs are about. I know it wasn’t good, so I don’t want to know. I put a high priority on staying happy, and I know what I can’t handle,’ via MTV.
She continued: ‘It’s not that I’m this egomaniac and I don’t want to hear anything negative, because I do keep myself in check.
‘But I’ve never developed that thick a skin. So I just kind of live a life, and I let all the gossip live somewhere else. If you go too far down the rabbit hole of what people think about you, it can change everything about who you are.’
October – December 2010: JAKE GYYLLENHAAL
Swift and Gyllenhaal made headlines when they dated for just three months in the fall of 2010, when he was 29 and she was 20
Swift and Gyllenhaal made headlines when they dated for just three months in the fall of 2010, when he was 29 and she was 20.
Sources told tabloids at the time that it was ‘serious,’ and they were even spotted together over Thanksgiving weekend.
Nearly two years after they split, Swift released Red, which included track number five, All Too Well, with allusions to the actor.
In the original lyrics, Swift sings about taking a trip upstate with her romantic partner, leaving her scarf at his sister’s house, dancing in the kitchen, and falling in love before it all ended.
She later teased on numerous occasions that the song as she originally wrote it lasted about ten minutes, but verses were cut for time.
Gyllenhaal, though, denied knowing anything about being featured on her album.
Earlier this year, Taylor released a 10-minute long, deeply personal version of All Too Well, which offered added new dramatic details in recounting their romance, singing that she was in ‘hell’ and felt ‘shame’ (pictured, the music video)
‘Do I [have a song]? I don’t know,’ he told Howard Stern in 2015.
July- October 2012: CONNOR KENNEDY
Taylor and Connor – the son of Robert F. Kennedy, Jr. and the late Mary Kennedy – were first spotted together at the Kennedy family home in Hyannisport in July 2012
Taylor and Connor – the son of Robert F. Kennedy, Jr. and the late Mary Kennedy – were first spotted together at the Kennedy family home in Hyannisport in July 2012.
But the summer romance barely lasted three months. Insiders said Taylor – who was four years older than Conor – freaked the 18-year-old by coming on too strong – and because of her apparent obsession with his famous family.
‘Conor’s just an 18-year-old kid and wasn’t ready for anything super serious,’ a pal told RadarOnline.com.
‘But Taylor is looking for her soulmate and it kind of freaked him out with how strong she came on,’ the insider went on.
The friend also said that Taylor was obsessed with the Kennedy family – and was living out a fairytale with Conor.
‘She was more obsessed with the idea of dating a Kennedy, than the actual Kennedy she was dating,’ the pal added.
The song would have firmly been in Swift’s past had it not been for the drama with her masters. In 2009, after Scooter Braun purchased her masters, Swift accused him of exerting ‘tyrannical control’ over her music, and the two had a bitter feud in the press.
At the urging of fans, Swift began rerecording all of the songs for which he owned the masters, which she has started to release — including several never-before-released tracks on each one.
She released a 10-minute long, deeply personal version of All Too Well, which offered added new dramatic details in recounting their romance, singing that she was in ‘hell’ and felt ‘shame.’
Most damning, though were revelations that Gyllenhaal told Swift the problem was their age difference.
‘You said if we had been closer in age maybe it would have been fine / And that made me want to die,’ she sings.
‘The idea you had of me, who was she? A never-needy, 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.’
Later, she quips: ‘And I was never good at telling jokes, but the punch line goes / I’ll get older, but your lovers stay my age.’
The line appears to be a direct dig at Gyllenhaal’s subsequent relationships, including his current one with French model Jeanne Cadieu — who at age 25 is 15 years younger than Gyllenhall, 40.
December 2012 – January 2013: HARRY STYLES
Fledgling couple Harry and Taylor dated from November 2012, with a source telling The Sun at the time: ‘Harry is head over heels for Taylor and even admitted he loves her while they were in the Big Apple.’
However they split just three months later in January 2013.
At the time it was reported she had ended their fling after an angry row during their New Year’s vacation.
He is largely believed to be the inspiration for her tracks Style and Out Of The Woods, both off of the album 1989.
In 2015, she admitted she always knew her relationship with Harry was doomed for fail.
In a video posted to celebrate the one year anniversary of her hit album 1989, she revealed that the number one feeling she felt during her three month fling with the One Direction singer was ‘anxiety’.
Before belting out a one-off acoustic version of Out Of The Woods, she elaborated on the relationship that inspired the song.
‘I’m going to play you a song that I wrote about a relationship that I was in that the number one feeling I felt in the whole relationship was anxiety,’ she explained as she sat at her piano.
Fledgling couple Harry and Taylor dated from November 2012, with a source telling The Sun at the time he was ‘head over heels’ for her
In 2015, she admitted she always knew her relationship with Harry was doomed for fail because she felt ‘anxious’ the whole time
‘Because it felt very fragile, it felt very tentative. And it always felt like, “Okay, what’s the next road block? What’s the next thing that’s gonna deter this?
‘How long do we have before this turns into just an awful mess and we break up? Is it a month? Is it three days?”
The former One Direction-er previously spoke about Taylor’s songwriting back in 2017.
He kept coy about the songs, but defended Taylor against critics telling Rolling Stone: ‘I mean, I don’t know if [Out Of The Woods and Style] about me or not, but the issue is, she’s so good, they’re bloody everywhere.
‘I write from my experiences; everyone does that.’
In 2020, Harry was asked by Howard Stern how he felt about exes writing songs about him, saying: ‘I think about what it means to me to write a song about somebody else and for somebody else to do that, it’s like flattering.
He went on, telling the shock jock: ‘Even if the song isn’t that flattering, you still spent time on it and ultimately, using Taylor as an example, she’s a great songwriter. So at least they’re good songs.’
Harry continued: ‘The only time you really think, “is this song too personal?” Is if you think about, “is this going to be really annoying for the other person?” Because I do [care].’
March 2015 – June 2016: CALVIN HARRIS
Taylor is rumoured to have started their relationship after meeting the hunk at a BRIT Awards after party in London in February 2015
Taylor is rumoured to have started their relationship after meeting the hunk at a BRIT Awards after party in London in February 2015.
However the couple ended up splitting in 2016 after a very public romance, with reports stating the relationship had ended because he was ‘jealous’ of the superstar singer’s success.
June – September 2016: TOM HIDDLESTON
The couple – formerly known as Hiddleswift – became infamous due to their enthusiastic public displays of affection
The couple – formerly known as Hiddleswift – became infamous due to their enthusiastic public displays of affection.
They shocked fans around the world after they were spotted locking lips on a beach in June 2016 – marking the beginning of their romance.
But the most infamous moment occurred during their July 4th weekend break in Rhode Island, where Tom was photographed frolicking in the surf with his lover while wearing a vest that was emblazoned with the message ‘I heart TS’.
Tom insisted that their relationship wasn’t a ‘showmance’ when talking to The Hollywood Reporter.
They shocked fans around the world after they were spotted locking lips on a beach in June 2016 – marking the beginning of their romance
‘The truth is that Taylor Swift and I are together, and we’re very happy,’ he said. ‘That’s the truth. It’s not a publicity stunt.’
The couple even took the huge step of meeting one another’s parents, with Taylor jetting to the UK to spend time with Tom’s mother in Suffolk, while he went to her adopted home town of Nashville.
However it was soon reported she put the brakes on the relationship after having regrets about how public the first few weeks were and getting the impression that Tom liked the limelight.
A source told Us Weekly: ‘Taylor knew the backlash that comes with public displays of affection but Tom didn’t listen to her concerns when she brought them up.
‘I think she feels a little embarrassed that the whole world saw them so serious and now it’s over.’
According to the publication, the pair were also struggling maintain a long-distance relationship, and met up in her Rhode Island home just last month in a bid to work through their problems.
They ended up breaking up in September of that year an insider exclusively told DailyMail.com that the pop star felt ‘uncomfortable’ with the actor’s desire to be ‘so public’ about their romance.
Tom had asked Taylor to the Emmy Awards that month, but she began questioning whether he was with her for ‘the right reasons’ and ultimately decided to call off the romance.
The actor commented in a GQ profile in a 2017: ‘Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time.’
He also nixed speculation the relationship was a stunt purely designed for publicity, insisting: ‘Of course it was real.’
He claims they were both seeking a normal relationship, adding: ‘So we decided to go out for dinner, we decided to travel… She’s incredible. [But] a relationship in the limelight… A relationship always takes work. And it’s not just the limelight. It’s everything else.’
He also finally explained the outfit he wore at her now famous July 4 party.
He claims he wore it just out of necessity, saying: ‘The truth is, it was the Fourth of July and a public holiday and we were playing a game and I slipped and hurt my back.
‘And I wanted to protect the graze from the sun and said, ‘Does anyone have a T-shirt?’ And one of her friends said, ‘I’ve got this.”
The friend pulled out the ‘I heart T.S.’ tank top that Taylor’s squad all own.
Tom explained: ‘And we all laughed about it. It was a joke.’
Indeed a source close to Taylor told People magazine that Calvin ended things with the Bad Blood hitmaker because he was ‘intimidated’ by her accomplishments.
‘[Harris] said on multiple occasions that he was intimidated by Taylor, which is why he would not attend any events where she was being honored, or any award shows unless he was nominated,’ the source added.
Moreover, The Sun reported that the pair wanted ‘different paths’, adding that ‘she ended her relationship with the musician because he would not commit to marriage and kids.’
The paper added that she wanted a long-term future, including living together and even starting a family.
While sources told TMZ, Calvin enjoyed their relationship initially because they both agreed to keep it private.
But later in the relationship the constant glare of the limelight made him uncomfortable as he disliked the unwanted attention.
Despite the initial heart break, the source is certain Taylor has put on a brave face: ‘Taylor is an independent young woman, and she realizes it will take a very secure man to handle her success.’
Meanwhile a source close to the Scottish DJ told People their romance fizzled due to coming ‘from very different worlds’.
The source said: ‘Their age difference might not be significant for many couples, but for them it was part of the problem too. Taylor somewhat lacks real-life experience.’
Then Calvin accused Taylor’s team of leaking that she had secretly written the lyrics for his hit track with Rihanna, This Is What You Came For.
He wrote soon at the time: ‘Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad at this stage though. I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do.
‘I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it. Please focus on the positive aspects of YOUR life because you’ve earned a great one. God bless everyone have a beautiful day.’
Calvin later admitted ‘all hell broke loose’ when he split from Taylor.
He told GQ: ‘It’s very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicised than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense. I’m not good at being a celebrity.
‘But when it ended, all hell broke loose. Now I see that Twitter thing as a result of me succumbing to pressure. It took me a minute to realise that none of that matters. I’m a positive guy. For both of us it was the wrong situation. It clearly wasn’t right, so it ended, but all of the stuff that happened afterwards.’
2016-Forever?: JOE ALWYN
Taylor began dating the Conversations With Friends star, 31, in late 2016 after they were rumored to have crossed paths at that year’s Met Gala in New York City.
The Lover singer reportedly kicked off her romance with Joe just months after her shock split from Loki actor, Tom Hiddleston, in September 2016.
Taylor gave fans insight into their burgeoning romance by alluding to Joe in lyrics on her hit 2017 album Reputation, including the song Gorgeous where she recalls ‘making fun of’ his English accent.
The Grammy Award-winner opened up even more on her 2019 album Lover, where she gushed about her ‘London boy’ on multiple tracks.
The song Cruel Summer is also rumored to be about the overlap between the beginning of her romance with Joe and the end of her fling with Hiddleston.
Joe told The Sunday Times in 2018 that he finds it ‘flattering’ that Taylor uses him as her musical muse.
Just two years later, Taylor welcomed her beau into the songwriting world by allowing him to pen lyrics for her 2020 alum, Folklore.
Using the pseudonym ‘William Bowery,’ Joe co-wrote two songs for the Grammy Award-winning album and three more songs for Folklore’s sister record Evermore.
Although she feels safe opening up in her music, Taylor previously stated that her relationship with the British hunk ‘isn’t up for discussion’ in the press.
She discussed the decision to keep their romance ‘private’ in her 2020 Netflix documentary Miss Americana, which included rare footage of herself and Joe.
She described ‘falling in love with someone who had a really wonderfully normal, balanced, grounded life’ and they ‘decided together that we wanted our relationship to be private.’
Though the pair have yet to make a red carpet debut, they’ve attended several high-profile events together – including the Golden Globes in 2020.
Whirlwind: Taylor began dating the Conversations With Friends star, 31, in late 2016 after they were rumored to have crossed paths at that year’s Met Gala in New York City; Taylor and Joe pictured in 2019
Privacy: The source also told The Sun that Taylor and Joe ‘want their love to stay away from the cameras as much as possible’ and that their alleged engagement is ‘just for them’; Taylor and Joe pictured in 2020
It emerged today the couple got engaged earlier this year, according to The Sun.
‘Taylor and Joe are incredibly happy, and very, very in love,’ a source claiming to be close to Joe told the outlet on Wednesday.
‘They’ve actually been engaged for a few months but have only told their inner-inner circle — basically immediate family, and trusted, very old friends.
‘Everyone has been sworn to secrecy, too.’
The insider alleges that Joe presented Taylor with a ‘beautiful ring’ but ‘she only wears it when she’s at home, i.e., behind closed doors.
Insight: Taylor gave fans insight into their burgeoning romance by alluding to Joe in lyrics on her hit 2017 album Reputation, including the song Gorgeous where she recalls ‘making fun of’ his English accent; Taylor and Joe pictured in 2019
Report: Taylor Swift has reportedly been engaged to boyfriend of more than five years, Joe Alwyn, for a ‘few months’; Taylor and Joe pictured in 2019
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