Though Olivia Wilde has had a few high-profile long-term romances – including with ex-fiancé Jason Sudeikis and ex-husband Tao Ruspoli – Harry Styles has stayed a little more low profile with his romances. He’s previously been linked to the likes of Taylor Swift and Kendall Jenner, though most of his relationships have been kept relatively private. In short, we know very little about his dating life. Until now. Sorta.
Styles and Wilde have been linked since they worked together on the film “Don’t Worry Darling,” which Wilde directed and Styles starred in, but the two have kept pretty low key about their relationship since late 2020. Though they’ve been spotted together numerous times since the first photos of them holding hands dropped in 2021, they haven’t given the public any concrete details about their love. Although we don’t know a whole lot about their relationship, we do know both have talked about how happy they are these days, and we can’t help but think they have each other to thank for that.
Ahead, find Styles and Wilde’s relationship timeline – from the time they began working together on “Don’t Worry Darling” until now – and follow along as they fall in love.
Getty / Mike Marsland / Dia Dipasupil
September 2020: Harry Styles Is Cast in Olivia Wilde's "Don't Worry Darling"
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.
Getty / Frazer Harrison
November 2020: Olivia Wilde Praises Harry Styles and Defends His Vogue Photo Shoot
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, “[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 defense. When conservative troll Candace Owens implied that Styles isn’t manly, Wilde simply replied by tweeting, “You’re pathetic.”
Getty / Jemal Countess
November 2020: Olivia Wilde and Jason Sudeikis's Split Goes Public
In November 2020, People reported that Wilde and her longtime partner Jason Sudeikis had called it quits. 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.
Getty / Robert Gauthier
January 2021: Harry Styles and Olivia Wilde Attend a Wedding Hand-in-Hand
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.
Getty / Stefanie Keenan
February 2021: "Don't Worry Darling" Wraps and Olivia Wilde Praises Harry Styles's Performance
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.”
Getty / Amy Sussman
Spring and Summer 2021: Harry Styles and Olivia Wilde Get Closer
Styles spent the beginning of 2021 filming the movie “My Policeman” in the United Kingdom, and Wilde spent 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.
Getty / Neil Mockford
July 2021: Harry Styles and Olivia Wilde Are Spotted Vacationing in Italy
In July 2021, Page Six reported that Wilde and Styles were enjoying a relaxing vacation 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.
Getty / Kevin Mazur
December 2021: Olivia Wilde Says She's "Happier Than She's Ever Been"
In her January 2022 Vogue cover story, Wilde opened up a little bit about her love life, saying, “I’m happier than I’ve ever been.” Of her relationship, she said, “It’s obviously really tempting to correct a false narrative. But I think what you realise 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.”
Getty / Kevin Mazur
April 2022: Harry Styles Says He's "Very Happy at the Moment"
While promoting the first single from his third album, “As It Was,” Styles made an appearance on Sirius XM’s “The Morning Mash Up” in April 2022. He said he was “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.”
