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A complete timeline of Harry Styles and Olivia Wilde's relationship

Olivia Singh   

A complete timeline of Harry Styles and Olivia Wilde's relationship
On the left: Harry Styles at the Grammys in March 2021. On the right: Olivia Wilde at the Vanity Fair Oscar Party in February 2020.Jordan Strauss/Invision/AP; Evan Agostini/Invision/AP
  • Harry Styles, 27, and Olivia Wilde, 37, have been romantically linked since January 2021.
  • They haven't commented on their speculated relationship, but have been photographed kissing.
  • Styles is set to appear in Wilde's next film "Don't Worry Darling," which she's also starring in.

September 11, 2020: Deadline reported that Harry Styles joined Olivia Wilde's upcoming movie "Don't Worry Darling," replacing Shia LaBeouf.

September 11, 2020: Deadline reported that Harry Styles joined Olivia Wilde
Harry Styles replaced Shia LaBeouf in "Don't Worry Darling."      Evan Agostini/Invision/AP

The publication reported that LaBeouf exited the project because of a scheduling conflict. But three months later, Variety reported that Wilde fired LaBeouf.

"Though shooting had not started yet when LaBeouf departed, insiders close to the project say LaBeouf displayed poor behavior and his style clashed with the cast and crew, including Wilde, who ultimately fired him," Variety reported in December 2020.

Wilde directed "Don't Worry Darling," which is described as a psychological thriller. The "Booksmart" director also stars in the film and serves as a producer. The star-studded cast includes Florence Pugh, Chris Pine, and Gemma Chan.

Wilde reacted to the casting of Styles and Pugh as Jack and Alice, respectively, by sharing a post on Instagram.

"Very proud to work with these fine folks," she wrote.

Production on "DWD" began in October 2020 but paused in November after a positive COVID-19 test on the set, Deadline reported.

In Styles' December 2020 Vogue cover, Wilde praised his performance in "Dunkirk" and said that the singer is "truly devoid of any traces of toxic masculinity."

In Styles
Olivia Wilde spoke to Vogue about being thrilled when Harry Styles signed on for "Don't Worry Darling."      Charles Sykes/Invision/AP

Wilde told the magazine that she was amazed by his "openness and commitment" to Christopher Nolan's movie, which also marked Styles' feature-film debut.

The actress also said that she and "DWD" costume designer Arianne Phillips "did a little victory dance" when Styles signed on for the movie "because we knew that he has a real appreciation for fashion and style."

"And this movie is incredibly stylistic," Wilde said. "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."

Wilde also called Styles "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.

Wilde added: "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 13, 2020: People reported that Wilde and Jason Sudeikis split and ended their engagement early that year.

November 13, 2020: People reported that Wilde and Jason Sudeikis split and ended their engagement early that year.
Olivia Wilde and Jason Sudeikis ended their relationship in 2020.      David Crotty/Patrick McMullan via Getty Images

News of the breakup emerged the same day that Styles' Vogue cover was released.

"The split happened at the beginning of the year," an anonymous source told People.

Wilde and Sudeikis' engagement was revealed in January 2013. They share a son named Otis and a daughter named Daisy.

"It's been amicable and they've transitioned into a great co-parenting routine," the source told People of the split. "The children are the priority and the heart of the family's relationship."

November 15, 2020: Wilde came to Styles' defense after conservative commentator Candace Owens criticized his Vogue cover, in which he wore a ruffled dress.

November 15, 2020: Wilde came to Styles
Olivia Wilde reacted to conservative commentator Candace Owens' comments about Harry Styles' Vogue cover.      Richard Shotwell/Invision/AP; Charles Sykes/Invision/AP

Owens called it an "outright attack" on "manly men." In response, Wilde tweeted her: "You're pathetic."

January 4, 2021: Page Six published photos of them holding hands at the wedding of Styles' manager, Jeff Azoff, sparking romance rumors.

January 4, 2021: Page Six published photos of them holding hands at the wedding of Styles
Harry Styles and Olivia Wilde attended a small wedding together.      JMEnternational/JMEnternational for BRIT Awards/Getty Images; Charles Sykes/Invision/AP)

Page Six posted a video and plenty of photos of the pair at the wedding in Montecito, California.

"They were affectionate around their friends, held hands and looked very happy," a source told People. "They have dated for a few weeks."

According to TMZ, there were only 16 people in attendance and Styles brought Wilde as his plus-one. Styles officiated the wedding, according to Entertainment Tonight.

A source also told Us Weekly that Styles referred to the actress as his girlfriend during his speech.

Photos published by Daily Mail UK shortly after showed the stars arriving at Styles' LA home with luggage.

They were also seen hanging out in Santa Barbara with some friends around that time.

February 15, 2021: Wilde praised Styles' work ethic after production wrapped on "DWD."

February 15, 2021: Wilde praised Styles
Olivia Wilde praised Harry Styles for his "humility and grace" on set.      Willy Sanjuan/Invision/AP

She posted a black-and-white photo of him in a classic car and gushed about his "humility and grace."

"Little known fact: most male actors don't want to play supporting roles in female-led films," Wilde's caption began. "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."

Wilde said that Styles was a rare actor who didn't mind taking a backseat to Pugh, his on-screen wife.

"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," she said. "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."

March 14, 2021: Wilde seemingly reacted to Styles winning his first-ever Grammy on Instagram.

March 14, 2021: Wilde seemingly reacted to Styles winning his first-ever Grammy on Instagram.
Harry Styles in his music video for "Watermelon Sugar."      Harry Styles/YouTube

Styles won the award for best pop solo performance for "Watermelon Sugar" and the 63rd Grammys. He also performed a jazzy rendition of the hit song at the award show.

That night, Wilde posted an old photo of Paul McCartney biting into a slice of watermelon on her Instagram story. The image was reminiscent of Styles biting into the fruit in his music video for "Watermelon Sugar."

Later that month, Wilde also commented a laughing emoji on a post from writer Evan Ross Katz, who reacted to Styles' portrait for Gucci's "Beloved" campaign and wrote: "Need a cinematic universe where it's Harry Styles and Allison Janney in bulky fur coats. We can figure out plot details at a later date."

The two stars spent time together in Europe in the months that followed.

The two stars spent time together in Europe in the months that followed.
Olivia Wilde and Harry Styles spent time together in the UK.      Mark Von Holden/Invision/AP; Charles Sykes/Invision/AP

According to the Daily Mail, they had a date night in West London in April. Meanwhile, Entertainment Tonight reported that Wilde was keeping Styles company in London as he filmed an upcoming movie called "My Policeman."

Additionally, ET reported that Wilde was in the UK to co-parent with Sudeikis, who was also in the area.

"Olivia is still in London, supporting Harry behind the scenes," a source told Us Weekly in May. "She gets a chance to bond with the cast when they're not filming but is more so excited to spend alone time with Harry when he's off set."

July 5, 2021: Page Six published photos of Styles and Wilde kissing on a yacht in Italy.

July 5, 2021: Page Six published photos of Styles and Wilde kissing on a yacht in Italy.
Their relationship was confirmed after Page Six posted photos of them kissing on a yacht.      Charles Sykes/Invision/AP; Charles Sykes/Invision/AP

The publication reported that the stars were in a scenic area called Monte Argentario

According to Us Weekly, it was Styles' idea for them to have a getaway before diving back into separate work projects.

"It couldn't be any more romantic," an anonymous source said. "It's been just the two of them and their bodyguards."

Days prior to showing full-on PDA, Styles and Wilde were seen walking through Italy with their arms around each other. They were also spotted dining together and attending the England vs. Ukraine soccer match at Stadio Olimpico in Rome.

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