One thing we can say about Olivia Wilde and Harry Styles’s 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 the 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 coparenting routine,” a source told People. “The children are the priority and the heart of the family’s relationship.” The ex-couple 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 are also photographed returning to 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
May 2022: Styles gives a rare statement about Wilde…just not about their romantic relationship. “I had a wonderful experience being directed by Olivia,” he told Howard Stern, per Page Six. “Acting is kind of very uncomfortable at times. I think you have to trust a lot. It requires a lot of trust if you want to kind of give it everything, and I think being able to trust your director is a gift, so that was very helpful.”
August 18, 2022: Styles and Wilde show off their boho couple style in NYC.
Harry Styles and Olivia Wilde in New York on August 18, 2022
MEGA
Later in the month, in an interview with Rolling Stone, Styles maintains he’s never been in a “public” relationship.“Sometimes people say, ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone,” he said. “If someone takes a picture of you with someone, it doesn’t mean you’re choosing to have a public relationship or something.”
He also calls out toxicity on social media and the pressure of dating as a pop star. “It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something,” he said. “I just wanted to sing. I didn’t want to get into it if I was going to hurt people like that.”
In the same interview, Wilde insists the “toxic negativity” comes from only a small faction of Styles’s fans. “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 told Rolling Stone. “I don’t personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness.”
September 5, 2022: Wilde and Styles arrive at the Venice Film Festival press conference for Don’t Worry Darling in separate boats.
They also stand separately in the cast red-carpet photos. Exhibit A:
Harry Styles, Gemma Chan, Chris Pine, and director Olivia Wilde attend the photo call for Don’t Worry Darling at the 79th Venice International Film Festival on September 05, 2022.
Getty Images
Exhibit B:
Olivia Wilde, Sydney Chandler, and Harry Styles attend the Don’t Worry Darling red carpet at the 79th Venice International Film Festival on September 05, 2022.
Stephane Cardinale – Corbis/Getty Images
That same month Wilde insists she didn’t leave her ex-partner for Styles. “The complete horseshit idea that I left Jason for Harry is completely inaccurate,” she told Vanity Fair. “Our relationship was over long before I met Harry.” Still, she remained coy about her relationship with the “As It Was” singer. “I think once you crack open the window, you can’t then be mad when mosquitoes come in,” she told VF. “It’s like, ‘You opened the window.’”
September 23, 2022: Don’t Worry Darling hits theaters.
October 2022: Wilde and Sudeikis’s former nanny gives an interview with dailymail.com detailing a dramatic fight between her employers over Wilde’s relationship with Styles in November 2021. According to the anonymous nanny, the incident ended with Sudeikis lying underneath Wilde’s car to stop her from delivering a salad with her “special dressing” to the pop star.
The former couple put aside their differences to release a joint statement condemning the interview on October 17. “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly,” they said. “Her now 18-month-long campaign of harassing us, as well as loved ones, close friends, and colleagues, has reached its unfortunate apex.”
Even so, Wilde trolled fans by posting a salad dressing recipe on her Instagram Stories the very next day.
November 15, 2022: Wilde is seen dancing with her eight-year-old son, Otis, and six-year-old daughter, Daisy, at Styles’s Los Angeles concert.
November 19, 2022: People reports that WildStyle is “taking a break” after two years. “He’s still touring and is now going abroad. She is focusing on her kids and her work in LA,” one source told the publication. “It’s a very amicable decision.”
November 22, 2022: Despite the “amicable” nature of the breakup, Wilde is reportedly “disappointed” that they couldn’t make things work. “The break has been difficult for Olivia,” a source told People. “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.”
As The Script once said: Hearts, they don’t break even.
This post may be updated.
Originally Appeared on Glamour
