Harry Styles' life after Olivia from partying with exes to Jen Aniston 'crush'
Harry Styles hailed 2022 as the 'year that changed my life', but 2023 already looks set to be a belter.
It's only February and already the former One Direction star has won a Grammy, beating the likes of megastars Beyonce and Adele.
And tonight he's set to perform at the BRIT Awards in London where he's nominated for Album of the Year, Artist of the Year, Song of the Year and Best Pop/R&B Act.
The last 12 months have certainly been a whirlwind for Harry, 29, after the release of his first major acting role in Don't Worry Darling.
It was while making the film that he fell for director Olivia Wilde, 38, who had recently split from fiancé, Ted Lasso actor Jason Sudeikis, 47.
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Harry Styles won Grammys for Best Pop Vocal Album and Album of the Year (Variety via Getty Images)The couple couldn't catch a break throughout their two-year romance amid rumours of on-set feuds with co-stars and much-denied tales of Jason begging Olivia not to see Harry.
And after being spotted looking tense on a night out in Los Angeles, on November 18 the pair confirmed they were 'taking a break'.
"He's still touring and is now going abroad. She is focusing on her kids and her work in LA," a source told People magazine.
"It's a very amicable decision. They're still very close friends.
"Right now, they have different priorities that are keeping them apart."
Harry Styles and Olivia Wilde met on the set of Don't Worry Darling (INSTAGRAM)
Olivia and Harry split after almost two years together (Corbis via Getty Images)While Olivia has since been seen enjoying a friendly hug with Jason, hinting at a thawing of relations, Harry is also said to have been in contact with his ex, Kendall Jenner.
Just four days before the split was announced, former flame Kendall was seen dancing at Harry's show with sister Kylie Jenner and their mutual friend Hailey Bieber.
And insiders say that Kendall - who has been linked numerous times to Harry between 2013 and 2019 - has been a source of support, especially given the recent end of her own relationship with basketball player Devin Booker.
"Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another. And Harry has had Kendall's ear over his break-up with Olivia," a source told The Sun.
Harry and Kendall Jenner have dated on and off for years (Getty Images for The Met Museum/)"Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time."
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Harry's debut solo album, Harry Styles, is said to have been largely inspired by his relationship with Kendall - something he has always refused to confirm or deny.
Without naming the woman in question, he said his ex had been a 'huge part' of the album, telling Rolling Stone: "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap... and hope they know it's just for them."
But despite their friendship, the same source said it's unlikely that the pair would ever get back together given how 'difficult' they found dating, coupled with the fact that, "all of those practical problems they faced years ago are still there."
Meanwhile, Harry also enjoyed a reunion with another ex - Taylor Swift.
Former flames Harry and Taylor were reunited at the 2023 Grammys (Getty Images)The former lovers dated from 2012 until 2013 and went on to pen a host of tracks about each other, from Taylor's Trouble and Style to One Direction's Perfect.
But there's never been any bad blood. Over the years, Harry has sung Taylor's songwriting praises at every opportunity and she put on a display of loyalty at the Grammys, giving him a standing ovation for his win and remaining on his feet as the crowd jeered over Beyonce missing out.
Later that evening, Taylor - who is rumoured to be engaged to actor Joe Alwyn - was spotted making her way over to Harry's table for a friendly chat.
Moving on, there's talk that Harry has another old woman in his crosshairs - his childhood crush Jennifer Aniston.
Harry and Taylor dated in late 2012 and penned numerous songs about each other (GC Images)According to reports, Harry sent Jennifer, 54, tickets to one of his gigs. It just so happened to be the one where he split his trousers on stage while performing Music For A Sushi Restaurant.
Apologising to the crowd, a red-faced Harry said: "My trousers ripped. I feel I must apologise to a certain few of you right down in the front there. I mean, this is a family show."
Jennifer was seen laughing in the audience and a source claimed Harry - who once told Ellen DeGeneres that Jen was his childhood crush - has the hots for her.
"Rumour is he personally sent Jen concert tickets because he's had a thing for her for at least two decades," a source told Australian magazine New Idea.
Harry Styles split his trousers in front of Jennifer Aniston (louistommo_org/Twitter)
Jen was Harry's childhood crush (Getty Images for The Hollywood R)"It's no secret Harry prefers older women."
So what about Olivia? Those claiming to be in the know reckon that neither have closed the door on it 100 percent.
"Harry will not say that they have broken up – just that they are taking a break and putting their relationship on pause," a supposed friend told Hollywood Life.
"No one thinks that they will resume the relationship after his tour, but Harry says that he does not know what the future holds."
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