When photographs of Harry Styles and Olivia Wilde holding hands hit the internet, it seemed as though the world was desperate to find out everything they could about the fledgling couple.
Here, we round up what we know so far about Harry Styles and Olivia Wilde’s relationship.
September 2020: Harry Styles is cast in Olivia Wilde’s new movie.
Deadline reports the news that Styles has replaced Shia LaBeouf in the forthcoming movie, Don’t Worry, Darling. Wilde serves as director on the project, with a screenplay from Katie Silberman, based on an original script by the VanDyke brothers. The movie costars Chris Pine and Florence Pugh, with Wilde taking a small role, too.
November 2020: Olivia Wilde describes her “victory dance” after casting Harry Styles.
Interviewed as part of Styles’s Vogue cover story, Wilde opens up about her reaction to casting the former One Direction member in Don’t Worry Darling. Wilde also describes the excitement she shares with Oscar-nominee, and the film’s costume designer, Arianne Phillips. “She 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 explained (via People). “And 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.”
“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,” Wilde said. “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.”
November 2020: Olivia Wilde splits from fiancé Jason Sudeikis.
In mid-November, news breaks of Olivia Wilde’s split from Jason Sudeikis, with People calling the breakup “amicable,” and noting the former couple’s dedication to their two children, son Otis Alexander, 6, and daughter Daisy Josephine, 4.
A source told People, “The split happened at the beginning of the year… It’s been amicable and they’ve transitioned into a great coparenting routine. The children are the priority and the heart of the family’s relationship.” Entertainment Tonight appeared to confirm this narrative, with a source allegedly close to Wilde calling the split “mutual.”
“They just fell out of love in a romantic way, but still have love towards one another as people,” the source explained to ET. “They consider themselves friends and co-parents first and foremost.” Another source added, “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.”
Wilde and Sudeikis were first romantically linked in November 2011, and Sudeikis proposed to Wilde just over a year later.
January 2021: Olivia Wilde holds hands with Harry Styles at a wedding.
In early 2021, photographs of Wilde and Styles holding hands surface online, and the internet erupts with questions. The new couple is spotted attending his agent’s wedding at the San Ysidro Ranch in Montecito, California.
An insider revealed to People that the new couple had been dating for some time. “They were in Montecito, California this weekend for a wedding,” a source told People. “They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks.” Twitter immediately mourns the fact that Styles is no longer a single man.
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.”
Further instances of PDA only seem to solidify their status as Hollywood’s newest power couple. A source also confirms to Us Weekly that Wilde and Styles worked hard to keep their relationship a secret during filming. “Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” Us Weekly‘s source revealed. “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.”
January 2021: Jason Sudeikis is subjected to conflicting reports.
It’s currently unclear how Wilde’s ex, Sudeikis, feels about her new relationship with Styles. A source claimed to ET that as Wilde and Sudeikis separated “almost a year ago… it’s not like she’s rushing into something.” The source continued, “Olivia and Jason talk all the time and are still close because of the kids. It’s highly unlikely he was blind-sided by this news.” Us Weekly‘s source concurs, saying, “Harry did not break up an engagement,” describing Wilde’s relationship with Sudeikis as “already done” by the time she met Styles.
However, People tells a very different story, with an insider claiming, “[Jason 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.”
January 2021: The pair’s relationship reportedly isn’t a PR stunt.
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.
“[The wedding photos were] absolutely not leaked or staged for some sort of promotional reason,” a source told the outlet, confirming that they were taken without the couple knowing.
The couple, who met on set of their upcoming film together, Don’t Worry Darling, also are reportedly having no issues balancing their professional and personal lives while on set. The source added that though the pair’s relationship isn’t a secret on set, it hasn’t gotten in the way of maintaining a “professional, collaborative and fun” work environment.
February 2021: Olivia and Harry are “very happy” together.
If anonymous sources are to be believed, then Styles and Wilde are still going strong. A source revealed to People that Wilde and Styles “seem very serious” and “spend all their time together.” The source explained, “[Olivia] is also very happy with Harry.”
As for how production on Don’t Worry Darling is going, the source told People, “Olivia and Harry continue to film in L.A. Filming has been tricky because of COVID. They have shut down the set several times for testing and breaks … Olivia is amazing to work with though. She stays calm and very focused despite all the breaks.”
February 2021: Olivia praises Harry on Instagram as Don’t Worry Darling wraps.
Director Wilde decided to share her admiration for Styles with the world by posting about him on Instagram. “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,” Wilde wrote. “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.”
The couple also posed for a photo with the rest of the cast as filming wrapped.
February 2021: Olivia and Jason rebuild their friendship as her romance with Harry grows.
A source at Entertainment Tonight said that, while Wilde is “so happy” in her new relationship with the One Direction alum, she and Sudeikis are now “in a good place, too.”
“Jason was initially really hurt about Harry and Olivia’s relationship, but now that he’s doing his own thing, things between him and Olivia have gotten better,” said the insider. “They’re rebuilding their friendship again and co-parenting together.”
March 2021: Olivia subtly supports Harry on Instagram after his first Grammy win.
At the 63rd annual Grammys ceremony, Styles won his first Grammy for Best Pop Solo Performance for his hit single, “Watermelon Sugar.” Wilde appeared to subtly show her support for him via her Instagram Stories, where she uploaded photos of some other music legends.
Wilde gave a shout-out to a Mick Jagger performance, in which he performed onstage wearing a leather jacket, a scarf, and not much else (in case that sounds familiar). She also posted a picture of Paul McCartney biting into a watermelon slice, which fans seemed to think was a pretty obvious nod to Styles’s Grammy-winning song.
April 2021: Harry and Olivia are getting a lot of “one-on-one time” in the United Kingdom.
A source for Entertainment Tonight revealed that the couple is spending time together across the pond.
“Filming during a pandemic in L.A. was pretty all-consuming,” the insider said of Wilde and Styles working together on Don’t Worry Darling. “Now they’re able to unwind, relax, and really enjoy some one-on-one time.”
The two have continued to keep a low-profile in the United Kingdom. “Their idea of a good time is going for a long walk and ducking into a neighborhood pub,” said the source.
Meanwhile, Wilde and her ex Jason Sudeikis have also mended their relationship and co-parenting dynamic. “All [Olivia’s] ever wanted is for them to have a united front,” another insider previously told the outlet. “They are and always will be a family.”
The duo, who dated for nearly a decade and were engaged, share two children together: seven-year-old son Otis and four-year-old daughter Daisy Sudeikis.
The second insider added, “She is proud of Jason and super supportive of him.”
June 2021: Harry and Olivia have “grown even closer as a couple,” a source says.
Speaking to ET Online, a source said that Styles and Wilde have been “having an awesome time” in London together where they’ve been “going on walks outside in the park and not hiding their relationship,” and have “grown even closer as a couple.”
“Yesterday, they enjoyed lunch outside and looked incredibly cute together,” the source added. “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.”
Watch this space for further updates!
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