Harry Styles And Olivia Wilde’s Relationship Timeline

For starters, it’s pretty clear the couple met on the set of Wilde’s sophomore feature-length directorial project Don’t Worry Darling, a 1950s-set psychological thriller starring the “As It Was” singer opposite Florence Pugh. Styles and Jenner split, however, in April 2016 after People confirmed the model had been dating Los Angeles Lakers player Jordan Clarkson. By September 2016, however, a source told People that Jenner and Styles were giving their relationship another try.

January 4, 2021: Harry and Olivia Are Spotted Holding Hands at a Friend’s Wedding

We are as shocked as anyone to see Harry Styles‘ fling-turned-romance with supermodelEmily Ratajkowski following their Tokyo-based make out sesh earlier this month. But perhaps no one is more surprised by it — or more dismayed, TBH — than the formerOne Direction frontman’s ex-girlfriendOlivia Wilde. After sitting on opposite ends of the room at a screening event for Don’t Worry Darling, the duo attended an afterparty for the film’s New York City premiere at The Bowery Hotel. Styles wore pinstriped pants with a double-breasted jacket, while Wilde opted for head-to-toe black.

February 2021: Olivia Praises Harry’s Work

Alyssa Bailey is the senior news and strategy editor at ELLE.com, where she oversees coverage of celebrities and royals . When she’s not working, she loves running around Central Park, making people take #ootd pics of her, and exploring New York City. While leaving a New York City gym in August 2022 ahead of a dinner date night. On September 21, Olivia was in the audience fangirling over her boyfriend as he wrapped up a 15-night set of shows at Madison Square Garden. While the couple have tried to keep their relationship under wraps, they were spotted packing on the PDA in Italy in July 2021. Experts agree that the time at home has forced singles to confront what they really want out of a relationship, and that means abandoning outdated tropes, like that a dude should be the older one in a partnership.

An eyewitness told The Mirror that the two had a dinner date outside with drinks. Filming began in mid-October with Wilde posting a photo of the Don’t Worry Darling director’s slate. Resurfaced video shared to TikTok shows Ratajkowski and Wilde together at a Styles concert in Paris last year. The One Direction alum performed at the Accor Arena on July 5, and there are Ratajkowski and Wilde swaying along. This was the first celeb-watchers have seen of this apparent new coupling — amid Ratajkowski’s post-divorce dating explorations and Styles’s split from Olivia Wilde, 39, last year amid their differing priorities — and, wow, what an introduction.

The filmmaker was previously in a long-term relationship with Jason Sudeikis. News that thetwo called off their engagementafter seven years together broke polyamorydate com chat in November 2020. A source told PEOPLE that the split “happened at the beginning of the year.” They share childrenOtis, 7, andDaisy, 5, together.

Her idyllic life begins to unravel when she suspects that things are not as they seem. After splitting from Wilde in November 2022, rumors abounded as Styles has moved on from the 39-year-old star and was seeing someone else. Further instances of PDA only seem to solidify their status as Hollywood’s newest power couple.

She added that there are misogynist undertones when people judge her based on paparazzi photos of her and Styles. “When people see me not with my kids, it’s always ‘How dare she,'” Wilde said. “I’ve never seen anyone say that about a guy. And if he is with his kid, he’s a fucking hero.” “I’ve never talked about my life away from work publicly and found that it’s benefited me positively,” he told the magazine.

During an interview with “Sprout” podcast, he was asked to delve intohis song “Cinema”— which describes the feeling of not being “cool” enough for a partner. That same month, a source confirmed to US Weekly that they were still going strong, despite having to spend time apart amid Styles’ travels on tour. The actress took to social media to subtly congratulate the singer on his Grammy win in March 2021.

From adorable PDA to gossipy red-carpet snapshots, Wilde and Styles certainly delivered a pop-culture moment. Yup, Olivia was spotted driving Harry’s pricey ride around LA while out with her friends, according to the Daily Mail. “I’ve been saying for literal months that they are VERY serious and no one ever wants to believe me.” We’ve all heard of a celebrity gossip account on Instagram named DeuxMoi, right? Well in April, speculation started to swirl that Harry and Olivia are engaged after DeuxMoi hosted a Q&A on their account. On August 18, Harry and Olivia also stepped out in style for a date night at Rubirosa Italian Restaurant in SoHo, New York City.

Harry Styles and Emily Ratajkowski’s surprise smooch weaves together one tangled celebrity dating web. It looks like Harry Styles has fully recovered from the flu, as he was seen enjoying a couple’s gym session with girlfriend Olivia Wilde on Friday, Nov. 11. Olivia was last seen supporting Harry when she attended his November 15 concert at LA’s Kia Forum, where she was accompanied by her two children. In addition to an oversized pair of black shades, the mother-of-two held onto a black hoodie and styled her hair into a single braid after working up a sweat inside. Wilde and Styles were actually seen at a west London pub last Wednesday. An eyewitness told The Mirror that they enjoyed dinner and drinks outside.

After he wrapped filming My Policeman in London, Styles and Wilde took an Italian vacation and were seen dancing, cuddling, and making out on a yacht off the coast of Monte Argentario. “She’s focused on her kids and co-parenting with Jason,” the insider said. “She and Harry are good friends, there’s no animosity whatsoever. Plus, she’s got many different directing projects in the works.”

Beyond the idyllic, 1950s bubble of the movie’s set, however, a lot of stuff went down in the real world during those four months of filming. Sounds like Olivia is juuust as excited as the fans about Harry’s casting news. In Harry’s cover interview with Vogue, Olivia reveals that she and the film’s costume designer, Arianne Phillips, are extra happy to have Harry around because of his love for fashion. Despite being separated by their respective work obligations, a source told Us that Wilde and Styles were still going strong.