They occasionally commented on their relationship and costarred in Wilde's film "Don't Worry Darling."
In November 2022, multiple outlets reported that the pair broke up.
September 11, 2020: Deadline reported that Harry Styles joined Olivia Wilde's movie "Don't Worry Darling," replacing Shia 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 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.
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."
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.
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.
"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.
January 4, 2021: Page Six published photos of them holding hands at the wedding of Styles' manager, Jeff Azoff, sparking romance rumors.
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."
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."
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.
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 with 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.
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.
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.
Fall 2021: Wilde supported Styles by wearing his merch and attending his concerts.
In addition to wearing similarly coordinated outfits while on walks together, Wilde was photographed on multiple occasions sporting items from Styles' merch collection (like the "treat people with kindness" hoodie, a Love on Tour t-shirt, and a Love on Tour jacket) and his gender-neutral beauty brand Pleasing while running errands.
In addition, Wilde appeared to wear Styles' gold-cross necklace to the Gucci Love Parade fashion show in Los Angeles in November 2021.
When Styles kicked off Love on Tour on September 4, 2021, in Las Vegas, Wilde was in attendance.
"She was so happy and dancing all night!" an eyewitness told E! News. "It was very cute. She was singing along to almost every song and having a good time with the people she was with."
Fans continued to notice the director at more of Styles' shows. At his San Diego show in November, Wilde was seen with her two kids and Styles' mom, Anne Twist.
December 9, 2021: Wilde vaguely spoke about her relationship with Styles in a cover story for Vogue.
"It's obviously really tempting to correct a false narrative," Wilde said regarding criticism of their relationship and 10-year age gap. "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."
Wilde added that she's "happier than I've ever been. And I'm healthier than I've ever been, and it's just wonderful to feel that."
April 15, 2022: Wilde supported Styles during his headlining performance at Coachella.
Weeks after being photographed walking through London's Soho area together, the couple headed to Indio, California for the festival.
As Styles performed during the first night of Coachella – and brought out surprise guest Shania Twain, Wilde cheered him on.
April 26, 2022: Wilde praised Styles' performance in "Don't Worry Darling" while presenting her film at CinemaCon in Las Vegas.
Wilde unveiled new footage of the thriller, applauded Pugh's performance, and jokingly called Styles "an up-and-coming actor with no other career that I am aware of."
"He is nothing short of a revelation in this part," she said.
May 18, 2022: Styles spoke about his positive experience working with Wilde for "DWD."
"Oh, wow, how to answer this question?" he responded, before pivoting to on-set interactions with her. "I had a wonderful experience being directed by Olivia. I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot."
"Being able to trust your director is a gift," he added.
August 22, 2022: In Styles' Rolling Stone cover, he and Wilde addressed the negativity aimed at their relationship.
"That obviously doesn't make me feel good," Styles told Rolling Stone, calling Twitter "a shitstorm of people trying to be awful to people."
"It's obviously a difficult feeling to feel like being close to me means you're at the ransom of a corner of Twitter or something," he added. "I just wanted to sing. I didn't want to get into it if I was going to hurt people like that."
When asked to weigh in from her perspective, Wilde called Styles' fans "deeply loving people" and said that the toxicity from others "is the antithesis of Harry and everything he puts out there."
"I don't personally believe the hateful energy defines his fan base at all," she said. "The majority of them are true champions of kindness."
In the same cover story, Wilde recalled Styles bringing the "DWD" crew "in tears" during one particular scene in which his character gets promoted at work.
Wilde said Styles went beyond what was asked of him and "took it to another level."
"He was so fully in the moment, he began screaming the lines to the crowd, in this primal roar, that was way more intense than anything we expected from the scene," she said.
August 24, 2022: In a cover story for Variety, Wilde spoke about casting Styles in "DWD."
Wilde called him the "perfect Jack," and Styles told the publication that "the story as a whole" attracted him to his role.
The musician also praised Wilde's work ethic.
"As a director, Olivia is incredibly focused," he said. "She communicated what she was looking for from the cast with both clarity and respect. I think transitioning from acting into directing has made her a director who knows how to get the best out of everyone."
Wilde also declined to comment on their off-screen romance because "I've never seen a relationship benefit from being dragged into the public arena."
"We both go out of our way to protect our relationship; I think it's out of experience, but also just out of deep love," she said.
September 5, 2022: Wilde and Styles attended the Venice Film Festival in support of "DWD," but had limited public interactions with each other.
At the film's press conference, red carpet, and screening that day, the stars were never positioned directly next to each other.
September 8, 2022: In a Vanity Fair cover story, Wilde shut down speculation that she left Sudeikis for Styles.
Wilde told the publication that "the complete horseshit idea that I left Jason for Harry is completely inaccurate."
"Our relationship was over long before I met Harry," she said. "Like any relationship that ends, it doesn't end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic."
September 19, 2022: Wilde and Styles attended an IMAX screening of "DWD" in NYC.
Styles and Wilde didn't stand directly next to each other during posed photos on the red carpet.
But fan-captured videos showed the couple leaving the theater together.
TMZ reported that Styles and Wilde attended the after-party together that night and "were together the whole time, hanging out and talking to each other."
November 18, 2022: Multiple outlets reported that the stars split after almost two years together.
Multiple sources confirmed to People that Styles and Wilde were "taking a break."
A source told the publication that it was "a very amicable decision," with the Styles touring abroad and Wilde "focusing on her kids and her work in LA."
"They're still very close friends," the source said.
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