A Timeline of Harry Styles and Olivia Wilde's Relationship

In 2018, the singer and model Camille Rowe parted ways after a year together. Following the break-up, Styles featured a voicemail from his former love on his album Fine Line, which was heavily inspired by their relationship.

On September 11, 2020, news broke that Styles had been cast in Wilde's upcoming thriller Don't Worry Darling to replace actor Shia LaBeouf. He will play opposite Florence Pugh as Jack and Alice, a 1950s married couple with stirring secrets. Shooting began in October, but production of the project was paused momentarily in November after a COVID-19 outbreak on set. 

For the "Watermelon Sugar" singer's December 2020 Vogue cover story, Wilde opened up about her shared excitement with the film's costume designer Arianna Phillips over Styles' casting. “[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," explained Wilde. "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.”

After nine years together, it was reported that the Booksmart director and actor Jason Sudeikis had broken up in early 2020. The couple, who got engaged in 2013, share two children together, Otis. 6. and Daisy. 4. An insider close to the couple told People, "It's been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship."

Monday, January 4, photos of the singer and actress holding hands while attending the wedding for Styles' manager Jeff Azoff together were released. People quoted a source that said the couple "have dated for a few weeks." According to Us Weekly, the former One Direction member even referred to Wilde as his "girlfriend" during a toast at the ceremony. 

While keeping their relationship a secret from the public, the couple leaned on friends like James Corden for support. “Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret," said a source at Page Six. "So everyone was really surprised—and rather delighted—when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.”

The Sun also reported on the burgeoning relationship, quoting a source about their attraction and how they couple with the 10-year age difference (Styles is 26, while Wilde is 36). “They clicked immediately—they’re both very artistic, passionate people and it was one of those things where straight away everyone could see they had a spark," said the insider, who also added, “Clearly they’re enjoying themselves and the age gap really isn’t a thing. Harry has obviously famously had a thing for older women but he’s just extremely mature himself, you’d never think there was a decade between them.”

Perhaps Styles' biggest supporter for his acting ventures, Wilde made an Instagram post a day after Valentine's Day praising the acting prowess and professionalism of her rumored beau. 

After spending a few months together in London, the duo were spotted being loved up on a yacht in Italy. 

After getting word of the couple's move from London to Los Angeles during the filming of Wilde's film Babylon, Styles and Wilde were spotted on a lunch date confirming their new location.

After Wilde made a post tagging Italian luxury brand Gucci, for which Styles is an ambassador, fans were quick to notice that same necklace being worn by Styles at one of his concerts. This comes a couple of months after Wilde was spotted having a great time at one of his shows in L.A.

Reports of the couple's holiday plans were shared with People, stating that Styles was getting closer to Wilde's kids — further solidifying the serious nature of their relationship.

During Styles' birthday celebration in London, Wilde posts a mirror selfie captioned with "Happy happy" in a '70s inspired jumpsuit on her Instagram story, presumably at the party.

The Don't Worry Darling cast appeared at the 2022 Venice Film Festival and the public immediately noticed weird placement and awkward tension between some members. After the drama around Shia LaBeouf being fired and then leaking messages and videos of Wilde begging him to come back to set—even though she claimed to be in solidarity with the film's star Florence Pugh—rumors started to circulate about the potential drama between Pugh and Wilde.

During this year's Venice Film Festival, Styles and Wilde weren't captured sitting next to or even talking to each other the whole time. With the behind-the-scenes drama and rumors, social media quickly questioned if the couple had broken up.

Regardless of what drama happened during the film festival, the couple's relationship seems to be in the clear. Wilde was spotted last night cheering on Styles as he performed the final show of his Madison Square Garden residency.