Harry Styles and Olivia Wilde's Relationship, From "Don't Worry Darling" to Coachella

On Sept. 11, 2020, Deadline announced that Styles had been cast in "Don't Worry Darling," a movie directed by Wilde. Styles was set to play the role of Jack across from lead actress Florence Pugh. Styles replaced Shia LaBeouf, who was originally cast in the role.

When Styles's Vogue cover story dropped in December 2020, it certainly stirred up some conversation. While many people were talking about the singer-actor wearing a dress on the cover of the magazine, others were reading quite a bit into Wilde's contribution to the story. On the topic of "Don't Worry Darling," Wilde told Vogue, "['DWD' costume designer Arianne Phillips] 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. 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."

It didn't stop there, though. When critics slammed Styles for what he wore in the photos, Wilde jumped to his defence. When conservative troll Candace Owens implied that Styles isn't manly, Wilde simply replied by tweeting, "You're pathetic."

In November 2020, news broke that Wilde and her longtime partner Jason Sudeikis had called it quits, according to People. The two had been together for a decade and spent seven years engaged. They share two children, Otis and Daisy. According to People, the split was amicable and reportedly happened at the beginning of 2020.

Wilde and Styles made their first public appearance as a couple at the wedding of Styles's manager and friend Jeffrey Azoff in January 2021. In exclusive photos and videos obtained by Page Six, the two were seen holding hands at the event. A source told Us Weekly that Styles referred to Wilde as his girlfriend at the wedding.

In February 2021, Wilde wrapped filming on "Don't Worry Darling" and shared sentiments on Instagram about the people involved with the project, including Styles. Alongside a black-and-white photo of him on set, Wilde praised his willingness to play second fiddle to Florence Pugh in the project. "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," she wrote, adding that Styles "infused every scene with a nuanced sense of humanity."

Styles spent the beginning of 2021 filming the movie "My Policeman" in the UK, and Wilde spent much of her time over there with him. The two were spotted around the UK several times, and sources told Us Weekly, Entertainment Tonight, and other outlets that the two were quite happy together and spending all their time with one another. Wilde also subtly supported Styles on his Grammy win with references to his outfit and winning song "Watermelon Sugar" on social media.

In July 2021, Page Six reported that Olivia Wilde and Harry Styles were enjoying a relaxing holiday in Italy. In the quite invasive photos of their yacht trip, the couple could be seen kissing, dancing, and generally enjoying each other's company on a break from work.

While promoting the first single from his third album, "As It Was," Styles made an appearance on Sirius XM's Morning Mashup in April 2022. Of creating the song, he said he's "really happy at the moment," adding, "I feel like it's the first time I feel like I'm kind of making music and putting music out from a real place of kind of personal freedom."