Harry Styles & Olivia Wilde’s Relationship: A Timeline

The pair met after the director replaced Shia LaBeouf, who left the cast of Don’t Worry Darling under what are still unclear circumstances, with the pop star taking over the role of Jack. “Very proud to work with these fine folks,” she wrote in an Instagram announcement, with which she also freshly announced Florence Pugh would be playing the film’s leading lady, Alice.

View this post on Instagram

A post shared by Olivia Wilde (@oliviawilde)

//platform.instagram.com/en_US/embeds.js

Don’t Worry Darling started filming in the fall of 2020 and wrapped in early 2021. At one point, the Booksmart filmmaker was photographed gazing down from the doorway of her trailer at Harry, who stood below her outside.

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.

https://www.instagram.com/p/CLSnTVRHPXZ

https://www.instagram.com/p/CLUtFsEgDwz

Just weeks before Harry and Olivia would be spotted together in public for the first time, word of the House actress’ split from fiancé Jason Sudeikis came to light when a source told People the news in November of 2020. The former couple had been together for seven years and welcomed two children — Otis and Daisy — during their time together.

The Ted Lasso star would later tell GQ that the breakup happened in November, though Olivia would go on to clarify that they’d ended their relationship toward the beginning of 2020.

It was the shot seen ’round the world — if by “shot,” you mean photograph, and by “the world,” you mean the internet. When a snap of the couple holding hands at a friend’s wedding surfaced online in January, one month before Don’t Worry Darling wrapped, frenzied fans and curious onlookers largely took it as proof that Harry had a new lady in his life.

After filming concluded for Don’t Worry Darling, Olivia took to Instagram to praise her cast on their performances — and naturally, it was her words on her rumored boyfriend that got people’s attention. “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 wrote of the singer. “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.”

https://www.instagram.com/p/CLUy-huHjLK

Sometime around June 2021, sightings of Harry and Olivia holding hands, going out to lunch and taking walks in London together started becoming more and more frequent. And in her Vogue cover story that October, the O.C. alum confirmed that she was officially living in the city.

“I’m finally driving a car,” she told the magazine. “I usually was in New York and not needing a car, but now that I don’t live there anymore and I live between L.A. and London, driving is now a thing where I’m like, ‘How am I going to participate in future innovation in a good way?’ I’ve been driving an electric car. And I’m like, ‘Ah, this does make me feel like a better human being.'”

Among the thousands in attendance at Harry’s April 2022 Coachella headlining performances was, of course, the actress-director. She was captured in fan videos cheering on her beau from the crowd, and later, the couple was filmed cuddling in the audience of Billie Eilish’s set.

Things got a little awkward for a second during Harry’s appearance on Howard Stern’s SiriusXM radio show, when the shock jock straight up asked him, “You fell in love on a movie set?”

The “Watermelon Sugar” singer skillfully redirected the question. “Oh, wow, how to answer this question? I had a wonderful experience being directed by Olivia,” he replied. “I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot.”

Harry’s long-awaited third studio record Harry’s House finally arrived in May of 2022, and fans were quick to speculate that several of its song lyrics seemed to be written about the director.

“Leave America, two kids follow her,” he laments on No. 1 lead single “As It Was,” potentially alluding to her two children with Sudeikis.

And then there’s a track literally called “Cinema,” which seems like an apt tribute to someone you reportedly fell in love with while filming a movie together, who also happens to be an actress and director. Then there’s also that little lyric “Darlin’,” which some believe may be a reference to their film Don’t Worry Darling. 

The Holivia sightings moved from London to New York around the time Harry’s Madison Square Garden mini-residency kicked off in late August. They’ve been seen walking the streets of the city, hitting the gym together, and grabbing dinner at an Italian restaurant — which they exited hand in hand.

Olivia discussed Don’t Worry Darling at the 2022 CinemaCon, where she shared a few kind words about Harry, calling him a “revelation” and joking that he was “an up-and-coming actor with no other career that I’m aware of.”

But the real talking point of the night came when a proxy on behalf of Jason Sudeikis served the director with custody papers while she on stage.

In the singer-songwriter’s August 2022 Rolling Stone cover story, both he and Wilde said their piece on the internet hate they’ve received in response to their relationship from a section of the Pleasing founder’s fanbase.

“That obviously doesn’t make me feel good,” Harry said. “Can you imagine going on a second date with someone and being like, ‘OK, there’s this corner of the thing, and they’re going to say this, and it’s going to be really crazy, and they’re going to be really mean, and it’s not real. … But anyway, what do you want to eat?’ ”

“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 continued.

Wilde added: “What I don’t understand about the cruelty you’re referencing is that that kind of toxic negativity 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. The majority of them are true champions of kindness.”

https://www.instagram.com/p/Chj510Yusos

Wilde also got her own cover in August 2022, with the Lazarus Effect star’s Variety issue featuring a cheeky reference to a lyric from her boyfriend’s Fine Line single “Golden.” During her interview, the director opened up about why she and the pop superstar don’t like to open up about their relationship.

“I’m not going to say anything about it because I’ve never seen a relationship benefit from being dragged into the public arena,” she told the magazine. “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.”

https://www.instagram.com/p/ChpYJzhspdR

View this post on Instagram

A post shared by Variety (@variety)

The Don’t Worry Darling cast’s appearance at the Venice International Film Festival was technically the pair’s first red carpet outing as a couple — though that was objectively outshined by a video appearing to show the pop star spitting on co-star Chris Pine (which the Wrinkle in Time star’s rep denied) and the director’s rumored feud with leading lady Florence Pugh.

Though the couple were never more than a few people apart, Wilde and Styles kept a professional distance throughout the event.

With being served legal papers on stage at CinemaCon still fresh in everyone’s minds, Wilde took a moment in her September 2022 Vanity Fair cover story to clear up rumors she left Sudeikis for her Don’t Worry Darling leading man.

“The complete horses–t idea that I left Jason for Harry is completely inaccurate,” she said. “Our relationship was over long before I met Harry. Like any relationship that ends, it doesn’t end overnight.”

“We were raising two kids during lockdown, so we co-parented through that time,” she added. “Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to not, because we could be better parents as friends who live in different houses.”

https://www.instagram.com/p/CiP3FOsOZXR

Just a few hours after she spoke with Colbert, Wilde headed over to Styles’ concert at New York City’s Madison Square Garden, where he was honored with a rare banner hung from the venue’s rafters commemorating his history-making Love on Tour residency of 15 sold-out shows.

She cheered him on in the audience, and at one point was dancing along to Harry’s House opening track “Music For a Sushi Restaurant.”

Two days before Don’t Worry Darling hit theaters, Olivia swung by The Late Show With Stephen Colbert to clear the air on everything from Shia Labeouf’s exit from the film to where she stands with Florence Pugh.

She also addressed her boyfriend’s viral “SpitGate” video for the first time. “I think it’s a perfect example of, like, people will look for drama anywhere they can,” she told Colbert, corroborating Pine’s rep’s assertion that Harry didn’t spit on the actor at the Venice Film Festival. “Harry did not spit on Chris.”

“I don’t feel like my male directing colleagues are answering questions about their cast,” she added. “[Male directors] are praised for being tyrannical. They can be investigated time and time again. It doesn’t overtake conversations about their actual talent or the films themselves.”