Finally, we have Olivia Wilde. Harry Styles and Wilde connected while working together on the latter’s feature film “Don’t Worry Darling” in late 2020, soon after she split from her longtime fiancé, Jason Sudeikis. Styles and Wilde were first photographed together as a couple in early 2021. According toPeople, the two connected on the movie’s set and were reportedly spotted hanging out in her trailer. At the time, Wilde had only good things to say about the pop star, telling Vogue, “To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has — truly devoid of any traces of toxic masculinity — is indicative of his generation and therefore the future of the world.”
The two continued to praise each other, with Wilde frequently complimenting Styles’ acting chops on her Instagram. The rumored relationship was pretty much confirmed when the stars were spotted smooching on a yacht in Italy that summer, but both continued to play coy.
When his relationship with Wilde came up on a May 2022 episode of “The Howard Stern Show” (viaPeople), Styles didn’t get personal. “I had a wonderful experience being directed by Olivia. I think there is something that obviously… acting is very uncomfortable at times,” he said. “Being able to trust your director is a gift.” And in the January 2022 issue ofVogue, Wilde didn’t say anything too specific about Styles, but she did state, “I’m happier than I’ve ever been.”