Simply Darling: Inside Olivia Wilde and Harry Styles' Surprising Love Story

Olivia Wilde found her leading man in more ways than one while making Don't Worry Darling, and Harry Styles can't stop singing her praises.

By Natalie Finn Sep 05, 2022 12:00 PMTags
Watch: Harry Styles & Olivia Wilde Address "Toxic Negativity" Amid Romance

It feels as if Olivia Wilde and Harry Styles went from "Hmm, that's random" to "Well, of course" in the blink of an eye.

But we're actually closing in on two years since cameras started rolling on Wilde's latest directorial effort, Don't Worry Darling, starring Styles and Florence Pugh as Jack and Alice, a comely couple who move to a utopian community in the California desert where something is seriously amiss. 

"We were all brought so close by the bubble of the production," Wilde told Variety ahead of the thriller's world premiere Sept. 5 at the Venice Film Festival. Though obviously some ended up much closer than others.

Wilde has said that she originally had Styles in mind to play Jack, having been very impressed by his acting debut in Dunkirk, but it wasn't until the pandemic put a halt to his 2020 tour plans that his schedule opened up. So, as fate would have it, she got her man (after Shia LaBeouf had exited the project under circumstances still being debated).

Harry Styles and Olivia Wilde's Romance Rewind

"We were looking for someone with innate warmth and palpable charm," Wilde told Rolling Stone for its September cover story on Styles. "The entire story depended on the audience believing in Jack."

After a six-month delay, filming got underway in October 2020 and continued—minus a pair of two-week pauses when someone on the production tested positive for COVID-19—through February 2021.

Though it wasn't public knowledge at the time, Wilde had split up with her partner of 10 years, Jason Sudeikis, closer to the beginning of 2020. News of their seemingly amicable breakup surfaced that November—and sparks were soon rumored to be flying between Wilde and Styles. 

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E! News later learned that the pair stayed in a rental home when they were on location in Palm Springs, utilizing the area's famed retro architecture, while most everyone else bunked at a hotel.

When Styles sported a full-length dress on the December 2020 cover of Vogue, Wilde championed his confidence and his sartorial choices, calling the "Sign of the Times" singer "truly devoid of any traces of toxic masculinity."

Recalling how she and Don't Worry Darling costume designer Arianne Phillips "did a little victory dance" when Styles came aboard, Wilde explained how they "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."

Harry Styles and Olivia Wilde Share Kiss in London

Needless to say, she was proud to be his date to the January 2021 wedding of his manager, Jeff Azoff, in Montecito, Calif. "They shared a room and did everything together" throughout the weekend," a source said. "They had a great time and are very happy."

But conveniently seeing each other all the time at work tends to be different than maintaining two separate showbiz schedules that can place significant others on opposite sides of the globe at any given time. 

Eh, maybe, but Wilde, 38, and Styles, 28, seem to be making it work. She's been spotted cheering and dancing at his concerts on multiple continents (including alongside his mom and sister at Wembley Stadium), they've done date nights in New York and carved out time to vacation in Italy—both last summer and this past May.

Harry Styles and Olivia Wilde's Italian Vacation

Not hurting matters was Wilde's need to spend significant time in the U.K. anyway to be with her and Sudeikis' kids while he was shooting Ted Lasso. Styles, as you might guess, keeps a home (and a yellow 1973 Jaguar) in London.

When Daisy, 5, and Otis, 8, are staying at Wilde's house in L.A., however, she builds her days around theirs. "They are my world," Wilde told Variety. "They are my best friends." (She's taken the children to see Styles in concert, but there's been no public visibility as a foursome, the kids' privacy being paramount.)

The last several months have been a lot, however, with the lead-up to Don't Worry Darling's premiere plagued by rumors of discord between her and Pugh (Wilde, who has raved about her leading lady's performance, would venture that there's generally a faction waiting in the wings to tear women down) and the experience of being served with custody papers right in the middle of her April presentation at CinemaCon leaving a bad taste in her mouth. (A source told E! Sudeikis had "no prior knowledge" of the timing.)

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So Wilde ultimately decided to take some time off instead of embarking on another directing project this summer.

"It became clear to me that this year was a time for me to be a stay-at-home mom," she told Variety. "It was not the year for me to be on a set, which is totally all-encompassing. It was time for me to pause and devote myself to the kids when I have them."

Needless to say, all eyes will be on the red carpet in Venice hoping for a certain duo's debut, but moviegoers will at least get to see the fruits of their labor when Don't Worry Darling opens in theaters Sept. 23.

Meanwhile, she and Styles have effusively supported each other in public without giving too much away, Wilde of course extolling his work in her film as her press tour heats up and the actor, in turn, calling her "a director who knows how to get the best out of everyone."

But as far as their romantic status goes, Wilde said, "I'm not going to say anything about it because I've never seen a relationship benefit from being dragged into the public arena. We both go out of our way to protect our relationship; I think it's out of experience, but also just out of deep love."

As Styles put it to Rolling Stone, "If someone takes a picture of you with someone, it doesn't mean you're choosing to have a public relationship or something."

Less in the spotlight when she was married to Tao Ruspoli for eight years before divorcing in 2011 ("I really had a sense that I had stunted my growth," Wilde told Amanda De Cadenet on The Conversation in 2012 of tying the knot at 19), the House star enjoyed relative privacy with Sudeikis—with an emphasis on relative considering the regular attention paid to their comings and goings as a unit. 

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Styles is the one who knows what it's like not to be able to go anywhere without being mobbed, to be sung about by Taylor Swift, and to trend on Twitter for the slightest little thing. So while he's used to that code-red tier of interest in his life, it stands to reason he wants to keep a little bit for himself.

"Can you imagine," he told Rolling Stone, "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?'"

As for her brushes with some of that craziness, Wilde told the magazine, "I don't personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness."

Without going into detail, Styles noted that any sort of negativity directed at his loved ones "obviously doesn't make me feel good."

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Critics of Wilde and Styles as a couple tend to follow the usual pattern of resentment that surfaces when hot 'n' famous people find each other. As in, there's rarely an actual reason for the vitriol, though naysayers can always come up with something.

An age gap, for instance.

"It's obviously really tempting to correct a false narrative," Wilde told Vogue for its January 2022 cover story. "But I think what you realize is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love."

Mind you, she never mentioned Styles by name. But, marveling over how "in the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us," she was done caring if the peanut gallery threw stones. 

"I'm happier than I've ever been," she said. "And I'm healthier than I've ever been, and it's just wonderful to feel that."

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