Look Back at Harry Styles and Olivia Wilde's Romance, From Film Sets to Possible Tattoo Tributes

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: "[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."

In November 2020, People reported that Wilde and Sudeikis, her longtime partner, 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.

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 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.

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.

When Styles took Love On Tour on the road across the United States in fall 2021, Wilde showed up at nearly every show. Fans spotted her on the fringes of many of the crowds, dancing along to Styles's music with his managers.

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."

During an August 2022 interview with Rolling Stone, Styles made some rare comments about his romantic life. He didn't name Wilde but did discuss the scrutiny that "the people closest to him," in Rolling Stone's words, can be subjected to. "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?'" he said. ". . . It's obviously a difficult feeling to feel like being close to me means you're at the ransom of a corner of Twitter . . . I just wanted to sing. I didn't want to get into it if I was going to hurt people like that."

Wilde was also interviewed for the Rolling Stone feature, and in it, she directly addressed the impact of Styles's fans' frequently cruel words about her. "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," she said. "I don't personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness."

Styles and Wilde made their red carpet debut on Sept. 5, 2022, while promoting "Don't Worry Darling" at the Venice Film Festival. They also stepped out at the film's premiere, though they were never photographed standing next to each other.

"Don't Worry Darling"'s release was shadowed by a slew of drama involving both the movie and Styles and Wilde's relationship, from rumors Wilde had left Sudeikis for Styles — which Wilde subsequently shut down — to controversy involving Shia LaBeouf's departure from "Don't Worry Darling," and much more.

In November 2022, according to People, Styles and Wilde decided to press pause on their romance. "The break has been difficult for Olivia," a source told the outlet. "They have had some issues, but Olivia thought they were gonna work through it all. She is disappointed. It's just a tricky situation, though."

In February 2023, a source told People that the pair had kept in touch. "They're still very close friends," the source said. "There's no animosity whatsoever. Plus, she's got many different directing projects in the works."

Styles was photographed in Italy in late July, and in the pictures, a tattoo that appears to read "Olivia" is visible on Styles's thigh. Styles is believed to have more than 60 tattoos, including a tribute to James Corden, so it wouldn't be too much of a surprise if he added another one in honor of Wilde at some point.