One thing we can say about Olivia Wilde and Harry Styles’ relationship is that it definitely happened! Whether or not you believe they were a PR couple joining forces to sell movie tickets, the 38-year-old director and 28-year-old pop star made plenty of headlines over the course of their on-set romance. 

The pair met on the set of Wilde’s film Don’t Worry Darling in October 2020 after the “As It Was” singer was brought in to replace Shia LaBeouf as the lead actor opposite Florence Pugh. According to multiple sources, their relationship quickly turned “romantic” and the rest is history. 

Nearly two years later, the couple is “taking a break,” but the decision may not have been as mutual as first reported. From that casting drama to the alleged salad-dressing fight, here’s a complete timeline of Harry Styles and Olivia Wilde’s relationship.

September 11, 2020: It’s announced that Harry Styles will replace Shia LaBeouf in Olivia Wilde’s feature film Don’t Worry Darling due to “scheduling conflicts.” For all the drama that unfolded later, click here

October 2020: DWD begins filming.

November 2020: Wilde announces that she and her fiancé of seven years, Jason Sudeikis, split toward the beginning of the year. “It’s been amicable and they’ve transitioned into a great co-parenting routine,” a source told People. “The children are the priority and the heart of the family’s relationship.” The pair share an eight-year-old son, Otis, and a five-year-old daughter, Daisy. 

Wilde also gushes about casting Styles in DWD for his Vogue cover story, saying she “did a little victory dance” when he officially signed on. “To me, he’s very modern,” she said, “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. I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.”

January 4, 2021: Photos of Styles and Wilde attending a wedding together go viral online.  A source told People, “They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks.” The pair were also photographed arriving back at his home in LA with their luggage.

According to a source that spoke to People, their relationship blossomed on the set of DWD. “What started out as a close friendship quickly turned romantic,” the insider said at the time. “Everyone saw it coming. During breaks, he wasn’t able to stay away and visited her trailer.”

March 15, 2022: The couple steps out in London hand-in-hand. 

Harry Styles and Olivia Wilde are seen in London on March 15, 2022.

Neil Mockford

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