But Styles jumped in without reservation to play backup to Florence Pugh’s leading role. “Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour.” Throughout the tour, Wilde was often spotted in crowds spanning the globe, most recently bringing her kids to see Styles in Los Angeles in mid-November.
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Their romance came two months after Olivia and ex-fiancé Jason Sudeikis publicly announced their split after being together for over a decade. A source told Us Weekly at the time that the “Sign of the Times” singer was not the reason for Olivia and Jason’s uncoupling. If the reviews were good, “Don’t Worry Darling” might have a chance to get people to focus away from the off-screen drama, which reportedly started when Wilde began a relationship with Styles during production. This affair may or may not have been a factor in Wilde’s breakup from Sudeikis, the father of her two children. Belloni also reported that Wilde’s focus on her new boyfriend bothered Pugh, while others on set said the romance also “annoyed” others because the couple weren’t always available on set when they needed to be.
And while Olivia attempted to brush the feud off by saying it was merely a case of the media pitting two women against one another, reports surfaced that Florence had “severely limited” her press commitments for the movie. Another important strand to the feud is that Olivia claimed that she fired Shia LaBeouf — who was subsequently replaced by Harry Styles — from the movie out of duty to Florence, who she wanted to ensure was “safe” and “supported” on set. The trailer for the film – directed by Harry’s girlfriend Olivia Wilde, 38 – sent fans into frenzy as Styles engaged in a number steamy scenes, which includes performing oral sex on Alice on the dining table, sharing a passionate kiss and in bed together.
As filming for Don’t Worry Darling started to wrap, the New York native took to social media to celebrate her cast. The couple’s romance continued to heat up, with the Life Itself actress openly supporting her beau’s music and film careers. She “obviously” watched his Eternals appearance, which she noted via an Instagram comment, and even danced — along with her kids and his mother, Anne, — at various “Love on Tour” concerts. “They’re still very close friends,” an insider tells People, adding that Wilde has been preoccupied with co-parenting alongside ex-fiancé Jason Sudeikis and embarking on new directorial projects. “There’s no animosity whatsoever. Plus, she’s got many different directing projects in the works.”
Though it was an amicable split and they claim to still be friends, Wilde is certainly not happy about who Styles is choosing to spend his time with post-breakup. “She is staying far away from this and taking the high road,” the source told the site of the Don’t Worry Darling director. She wants nothing to do with this mess.” Another source told Us Weekly that Olivia “is trying not to be jealous because she is moving on as well.” The source also said that the makeout video “upsets” Wilde.
In May 2017, the pair were spotted spending time together in London, with sources sharing that Styles and Ward had already been on “a number of dates” by then. That month, Ward put rumors into overdrive when she wore the same shirt as Styles to an event. He dated Olivia Wilde for well over a year, only just breaking up with the actress and director in November 2022.
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“Sometimes people say, ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone,” he said. “I also feel really happy at the moment and I feel like it’s the first time I feel like I’m making music and putting music out from a real place of personal freedom,” he shared. “And that is a really liberating place to [be] creating from and now putting it out.”
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“We were never boyfriend and girlfriend. I think that’s the first time I’ve ever admitted to what it was because I’ve always just shrugged it off before,” she told Reveal magazine. “It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season. After that, anyone could say anything. In the street, people started shouting at me ‘pedophile’ and ‘pervert,'” she further explained. The actress died in February 2020, aged 40, after she hung herself in her London home.
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Sources told PEOPLE there was a lot of “flirting and smiling going on.” In February, they celebrated Styles’ 20th birthday together. “Kim and Harry looked like they were enjoying each other’s company,” a source told PEOPLE. She had only been dating him for a few weeks when they had their courthouse wedding. Ratajkowski gave birth to their son in March 2021, but a year later she separated from her husband. The model and actress has since come forward to reveal Bear-McClard’s infidelity as the cause for their divorce.
“Don’t worry,” Wilde captioned the post, referencing the title of the film that she directed and stars in. Ratajkowski had also spent a lot of time with Styles and his ex Olivia Wilde throughout their nearly two-year romance, which added to the surprise of their kiss. “I’m hoping that dating someone that has more of their own life will prevent the issues I had before,” she said, not so subtly alluding to her estranged husband Sebastian Bear-McClard, with whom she shares 2-year-old son Sylvester. “Coachella prep,” she wrote via her Instagram Story alongside a video clip of the ’70s duo Baccara dancing to their 1977 hit “Yes Sir, I Can Boogie.” Though she didn’t mention Styles by name, fans were quick to put together the clues. “It’s obviously really tempting to correct a false narrative,” she said. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about it. All that matters to you is what’s real, and what you love, and who you love.”
The couple is still going strong — most recently, the Booksmart director was seen supporting the former One Direction member at his Harryween concert, dressed as Dolly Parton. Jenner’s not the only model in Styles’ dating history; he’s also been linked to such Victoria’s Secret angels as Nadine meet-an-inmate Leopold, Sara Sampaio, Georgia Fowler and Camille Rowe. A friend of the couple explained, “Right now, they have different priorities that are keeping them apart.” The pal added, “The public pressure on them has been difficult. They’ve had ups and downs throughout the relationship.”
A source revealed to Entertainment Tonight that Wilde and Styles’s budding romance is the real deal, explaining that the wedding photos that first leaked confirming their relationship were not staged in any way. Meanwhile, a source revealed to Entertainment Tonight that Wilde and Styles got to know each other on the set of Don’t Worry, Darling, and their romance blossomed from there. “Olivia and Harry are together for long days on set and have gotten to know each other really well, so it’s all very organic,” the source revealed. “[Olivia] wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.” “They just fell out of love in a romantic way, but still have love towards one another as people,” the source explained to ET.