When Harry met Taylor – why the latest starlet on the superstar’s arm could take his solo acting career to new heights
HARRY Styles has been in and out of relationships since he shot to fame as one fifth of boyband One Direction.
From X Factor teen wannabe to global solo heartthrob and now a leading man in Hollywood, Harry's career has gone from strength to strength.
But it's his personal life and relationships which have garnered the most attention.
Here, we look at the women who have captured his heart as he begins a new relationship with Canadian actress and model Taylor Russell, and our experts give us a Sign of the Times about what it really means in the latest stage of Harry's whirlwind personal life.
Taylor Swift - The superstar romance
This was his first superstar romance after One Direction shot to fame.
He met Taylor in March 2012 backstage when they were both performing at the Kids Choice Awards.
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A few months later they were spotted strolling through New York's Central Park, wrapped up in winter coats and even wearing matching dark blue jeans.
At Tay's 23rd birthday, Harry introduced her to his mum with the trio even photographed feeding the birds.
But they called it quits in January 2013 after a series of blazing arguments following a Caribbean holiday which saw Taylor heading home alone.
Still, there's no bad blood with the stars still great pals to this day.
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Kendall Jenner - The one that got away
Harry and supermodel Kendall have been linked romantically multiple times with the pair reportedly hooking up in 2013 and again, in 2016.
The couple's romance blossomed on the ski slopes in January 2014, followed by a Caribbean trip in December 2015 with Kendall's sister Khloe confirming they were an item.
But it was Kendall who seemed to cool time on their relationship with sources saying she wanted to settle down and he didn't.
This is despite the singer revealing she was his muse for his May 2017 debut studio album saying: "She's a huge part of the album."
The two still seem to be good friends and lovingly joke about their previous flings.
In a 2019 appearance on The Late Late Show With James Corden, Kendall asked Harry, "Which songs on your last album were about me?"
The musician chose not to answer the question.
She later supported Harry at a concert in Los Angeles with a video shared by fans on social media showing Harry blowing Kendall a kiss during his performance of "Love of My Life," - with fans speculating it was about her.
Tess Ward - The low key blogger
After all the attention that his previous relationships garnered, Harry dated unknown food blogger Tess Ward in 2017.
They couple enjoyed a string of dates in London with Harry introducing Tess to his stylist Lou Teasdale.
Even though the two reportedly shared clothes their relationship was fleeting.
Two months after headlines broke that they were in a relationship, they went their separate ways, proving a low key relationship just isn't for Hazza.
Olivia Wilde - The grown up phase
Harry wasn't shy about his romance with Hollywood star and director Olivia with the couple stepping out in public as a couple after Harry starred in Olivia's directorial debut Don't Worry Darling.
In November 2020, Wilde said she did a "victory dance" when she heard Harry had been cast in the film.
A few weeks later Olivia split from Jason Sudeikis, with People calling the breakup "amicable," and noting the former couple's dedication to their two children.
Then, in January 2021, Olivia and Harry held hands at a wedding with sources saying they've been dating for weeks and fell for each other during filming.
The romance blossomed into 2021 with Olivia spending time in the UK, supporting Harry at gigs and sharing clothes.
By the end of the year she had introduced Harry to her kids whom she shares with ex Jason Sudeikis while 2022 saw the premiere of Don't Worry Darling and the couple continued to support each other in the public eye.
But then in November that year they announced, after nearly two years together, their split.
It was Harry's longest relationship and had even seen him play family man.
Emily Ratajkowski - The fun fling
After a heavy romance with Olivia, Harry had some fun with supermodel Emily in March 2023.
The pair were spotted snogging and cuddling in a car park in Tokyo with Emily - who had split from husband Sebastian Bear-McClard in July 2022 - later saying: "I'm definitely still not thinking about guys...although, yeah.
"You know, sometimes things just happen."
But a source added: "Emily isn't looking for anything serious.
"She's just trying to live her best single life and have fun."
It emerged that in July 2022 Emily attended one of his concerts with his then girlfriend Olivia.
Taylor Russell - The critically acclaimed stage
With his star rising in Hollywood, Harry is head over heels for Canadian critically acclaimed actress Taylor Russell, 29.
The starlet recently starred in 2022 film Bones And All, alongside Timothee Chalamet, where she received a nomination for Best Lead Performance at the Independent Spirit Awards.
In June, the couple were spotted together for the first time as they exited a museum in London.
She then attended his Love On Tour concert in Vienna.
They have since been spotted at various different events in London with Harry supporting Taylor at the opening of her new theatre show The Effect at the National Theatre.
When they first crossed paths is still unclear, but they both attended the 79th Venice International Film Festival last year in September 2022 where Harry was promoting Don't Worry Darling, while Russell celebrated the premiere of Bones And All.
Is this a sign that Harry wants to focus on his acting career and make a new Hollywood power couple with Taylor?
Caroline Flack - The older woman
Harry and the Love Island host's relationship caused a stir back in 2011.
They met when she was a presenter on The Xtra Factor and were romantically linked when Harry was spotted leaving her house.
Caroline wrote in her autobiography Storm in a C Cup that because of the age difference – she was 31; him 17 – she received death threats from Harry's fans and abuse in the streets.
In August 2011 Harry told the official X Factor website: “If Caroline Flack is reading this, say ‘Hi’ from me. She is gorgeous!”
According to reports, Harry's dream finally came true when he revealed his feelings to Caroline about at an X Factor party at the W Hotel in London that October.
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After three months together the pair parted ways in January 2012 with Harry rumoured to be devastated.
But it became one of his defining relationships, and set the tone for his love of older women with him going on to date cougars Olivia Wilde and Nicole Scherzinger.
