Each year offers a handful of surprising celebrity couples to analyze, 2021’s first arrived early with the new romance of Olivia Wilde, 36, and Harry Styles, 26. They met while she was directing him in the upcoming film Don’t Worry Darling. Multiple outlets reported that the celebs were an item after they held hands at his manager’s wedding earlier this year.
Their offscreen relationship arrives following Wilde’s split from longtime fiancé Jason Sudeikis after nine years and two children—seven-year-old Otis and four-year-old Daisy. As for Styles, his love life before meeting Wilde was characterized as “pretty nonexistent during lockdown” by an Us Weekly source. Consider his dating drought over. Ahead, everything we know about Styles and Wilde’s relationship, including their movie meet-cute and what their spring and summer in London has been like.
September 11, 2020
News broke that Styles had been cast in Don’t Worry Darling, Wilde’s directorial follow-up to 2019’s Booksmart. Styles reportedly replaced Shia LaBeouf following his “poor behavior” and violation of Wilde’s “zero asshole policy” on set, a source told Variety. Although earlier reports cited a scheduling conflict for LaBeouf’s departure, his exit also came amid his ex-girlfriend FKA twigs’s lawsuit against him on charges of “sexual battery, assault, and infliction of emotional distress.”
Wilde announced Styles and Florence Pugh’s casting on Instagram, writing, “Jack and Alice. Very proud to work with these fine folks. #DontWorryDarling.”
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October 15, 2020
Filming began in mid-October with Wilde posting a photo of the Don’t Worry Darling director’s slate. “Blank slate. Full heart. Let’s do the damn thing, @libatique. 💪 #pressureisaprivilege,” she captioned the post.
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November 13, 2020
The first time Wilde publicly spoke about Styles was for his cover interview with Vogue. “To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has—truly devoid of any traces of toxic masculinity—is indicative of his generation and therefore the future of the world,” she said in the profile. “I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.”
She also spoke about the moment she and the film’s costume designer, Arianne Phillips, found out Styles would be joining the cast. “She [Arianne] and I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style,” Wilde told the outlet. “This movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that he is so enthusiastic about that element of the process—some actors just don’t care.”
If those weren’t ringing endorsements enough, Wilde also defended Styles’s gown on the cover against conservative commentator Candace Owens. After Owens said, in part, “Bring back manly men,” Wilde replied, “You’re pathetic.”
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January 4, 2021
Only a few days into the year, Styles and Wilde’s relationship was revealed at his manager Jeffrey Azoff’s wedding. The pair was photographed holding hands in masks by The Vampire’s Wife, he in a black suit with white ribbon and she in a pastel floral dress. People reported that Wilde and Styles were, in fact, a couple after meeting on the set of Don’t Worry Darling. “They were in Montecito, California this weekend for a wedding,” a source explained. “They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks.”
Meanwhile, an insider told TMZ that Styles officiated Azoff’s wedding and brought Wilde as his plus one to the wedding. Per the outlet, the couple looked “very much together” at the nuptials, attended by just 16. The Sun’s source said that Wilde and Styles “clicked immediately—they’re both very artistic, passionate people and it was one of those things where straight away everyone could see they had a spark. It’s no surprise something has happened, but now they’re quite open about it and out and about as a couple. They went to a wedding together with a lot of their friends there.”
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January 5, 2021
The following day, several outlets had intel on Styles and Wilde’s dynamic, which ELLE rounded up. A source told Us Weekly that Styles had referred to Wilde as his “girlfriend” during a speech at the wedding. Another source said the pair “had chemistry almost instantaneously on set [of Don’t Worry Darling]. It was only a matter of time before they got together.”
A Page Six source claimed that none other than James Corden helped facilitate the relationship by allowing Styles and Wilde to stay at his California home while shooting their movie. “Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret,” the outlet’s source said. “So everyone was really surprised—and rather delighted—when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.”
Meanwhile, a source told Entertainment Tonight that Wilde “wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.” The insider also claimed that “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.” As for implications that Wilde moved on too quickly with Styles following her Sudeikis breakup, the source said that they split early in 2020, although the news wasn’t announced until November. “Olivia and Jason talk all the time and are still close because of the kids,” the source added. “It’s highly unlikely he was blind-sided by this news.”
January 7, 2021
Photos emerged of Styles and Wilde out and about in Santa Barbara. Both were masked up as Styles put his arm around Wilde. He wore a pink beanie, bandana, and black hoodie. She wore dark brown pants, a white mask, and a tan argyle sweater.
January 8, 2021
When Sudeikis and Wilde’s split was first revealed, a source told People that the breakup was “amicable and they’ve transitioned into a great co-parenting routine.” Entertainment Tonight further reported that the couple “just fell out of love in a romantic way, but still have love towards one another as people,” per a source. Another insider added that “there was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.”
But after her romance with Styles became public, a source told People that Sudeikis “is absolutely heartbroken about the split. There is still a lot of love there, and he would like to have hope that maybe there’s a way for them to repair things. But what happens next remains to be seen.” A Page Six source went one step further, claiming that Styles and Wilde had been dating for longer than “the past few weeks.” The insider said, “Jason found out about Harry and pushed the conversation. Olivia then asked for a separation and news of the split was made public.” Neither party has commented directly on reports concerning their breakup.
January 9, 2021
It’s unclear when exactly things turned romantic between Wilde and Styles. But a source told Us Weekly that they “were able to keep their relationship under wraps for a bit before it became public knowledge,” adding, “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.” The insider further clarified that “Harry did not break up an engagement.”
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January 10, 2021
Another day, another conflicting report about the timeline of Sudeikis and Wilde’s split: “Olivia called off the engagement in early November but only after she already had gotten close to Harry,” a source told Us Weekly. “Whether Harry knows it or not, he was a reason for the split and it blindsided Jason—he totally adores Olivia and is devastated. Family is his biggest priority.”
Still, another source insisted that “the engagement was called off early last year, as was previously reported. Harry was in no way the reason for their split.”
February 14, 2021
On Valentine’s Day, Wilde posted a tribute to Styles, ostensibly about his role in Don’t Worry Darling.
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She wrote:
Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our ‘Jack’. Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our ‘Alice’, but he infused every scene with a nuanced sense of humanity. He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards. 👊 #dontworrydarling.
February 17, 2021
E! reported that the duo traveled to London together on February 16 after wrapping production on Don’t Worry Darling.
“Harry and Olivia loved being on the road and have gotten very comfortable spending all of their time together,” a source told E! “They are rarely apart and it made sense to go to London together.”
Wilde’s two children were in London with Sudeikis and she planned to spend time with them. “Olivia will mostly be spending time with her kids while Harry sees family and friends,” the source added. “He also wants to show her around and go to some of his favorite spots.”
April 14, 2021
After two months out of the spotlight, Styles and Wilde were seen at a west London pub. An eyewitness told The Mirror that the two had a dinner date outside with drinks.
“They looked very cozy on an intimate table for two away from other diners,” the source said. “They were grinning like Cheshire cats at each other all night.”
The two appeared pretty in love, the source added: “[Olivia] had her legs crossed and gently nudged against him. They looked completely smitten.”
April 21, 2021
Entertainment Tonight got an update from a source about how Wilde and Styles’ time in London has been. The couple, the source said, have deliberately avoided public places and keep a low profile. “Their idea of a good time is going for a long walk and ducking into a neighborhood pub,” the source said.
The two have enjoyed having more downtime now that their film Don’t Worry Darling has wrapped. “Filming during a pandemic in L.A. was pretty all-consuming,” the source said. “Now they’re able to unwind, relax, and really enjoy some one-on-one time.”
June 4, 2021
Entertainment Tonight got a rare look at Wilde and Styles’ relationship in London—and confirmation the two are still going strong as summer begins. The outlet ran a photo of the two on a lunch date together. A source spoke to Entertainment Tonight about how well things are going between them.
Wilde and Styles are “having an awesome time [in London],” the source started. “[They’ve] been going on walks outside in the park and not hiding their relationship [and have] grown even closer as a couple.”
“Yesterday, [June 3], they enjoyed lunch outside and looked incredibly cute together,” the source said. “They were both in a great mood and left the restaurant holding hands. Harry put his arm around Olivia as they walked back to her house.”
Later in the month, they were seen on what was reportedly a vacation in Italy, following their time in London.
“Harry has been seen taking a break on the beach in Porto Ercole after he finished filming My Policeman in London,” a source told Page Six.
Following the vacation report, a source told Entertainment Tonight that what Wilde and Styles have is “not a short fling.”
“It’s obvious that this was not a rebound or a short fling,” the source said. “They care so much about each other and have a deep connection.” The source continued: “They’re pretty low-key and have enjoyed being somewhat out of the public eye.”
December 9, 2021
Wilde did her first in-depth interview since starting to date Styles with Vogue. The actress demurred from speaking at detail about him or their relationship, but she did address the scrutiny she received for their 10-year age gap and how happy she is now.
“It’s obviously really tempting to correct a false narrative,” Wilde said of those critical of a woman in her 30s dating a man a decade younger. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love.”
“In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us,” she added. “[But] I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that.”
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