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Why Olivia Wilde and Harry Styles' Romance Makes Perfect Sense

Harry Styles finds girlfriend Olivia Wilde immensely talented. She thinks his feminism is sexy. And those are just two reasons why the pair's budding romance is headed in the right direction.

By Sarah Grossbart Mar 10, 2021 4:00 PMTags
Watch: Harry Styles & Olivia Wilde's Relationship Timeline

You know that well-worn adage about how the way to a man's heart is through his stomach? The one your grandma may have trotted out while teaching you some essential family recipe? 

Well, the way to Olivia Wilde's heart appears to be through acts of feminism. Because when now-boyfriend Harry Styles signed on to her upcoming film Don't Worry Darling, jumping at the chance to appear in a supporting role opposite British actress Florence Pugh, color her impressed. 

"Little known fact: most male actors don't want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles," the director revealed in a Feb. 15 Instagram. "No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our 'Jack.'"

Letting Pugh "hold center stage," Wilde continued, "he infused every scene with a nuanced sense of humanity. He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards."

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25 Things to Know About Harry Styles

Color her verrrrry impressed. 

Because not long after the 27-year-old former boy bander signed on to become their Jack, he became Wilde's guy. With the actress single for the first time in nearly a decade, following her early 2020 split with former fiancé Jason Sudeikis, she and the three-time Grammy nominee engaged in some light flirting on the Palm Springs set after filming began in November, a source revealed to E! News.

Their chemistry "very obvious," as a source put it to People, soon Styles was popping into her trailer for extended chats. Noted the source, "Everyone saw it coming."  

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Those not in the know were clued in shortly after New Year's Eve when Wilde turned up as Styles' date to manager Jeff Azoff's Montecito, Calif., vows, the pair photographed hand-in-hand in all their wedding finery. And just like that, mere weeks into their romance, suddenly they were a thing

"They have gotten serious quickly and have an intense connection and bond," a source told E! News of the pair, who spent much of the winter bunking together at a Hollywood Hills pad. (That is, when she wasn't with her kids, son Otis, 6, and daughter Daisy, 4.) "They don't want to be away from each other at all."

So they haven't really, transitioning from Don't Worry Darling's California sets to Styles' preferred stomping grounds in London where he splashed out for a fixer-upper at 18, not long after a chance tryout for The X Factor led to him being part of one of the biggest boy bands of all time.  

Having spent the last stretch of the shoot in Barstow, Calif., "Harry and Olivia loved being on the road and have gotten very comfortable spending all of their time together," the source told E! News. And with Wilde afforded a bit of time off, "It made sense to go to London together."

Across the pond they have tended to separate responsibilities. Wilde has spent time with her kids while ex Sudeikis films the second season of his surprise comedy smash Ted Lasso (with new flame Keeley Hazell) and Styles has visited friends and family. 

But the Brit, who grew up in the village of Redditch, a place he told Vogue "truly felt like a different country" than London, had every intention of stealing her away for stretches of time.

"She and Harry have had a great time in London taking it easy and enjoying time off," continued the source. With Styles attached to two upcoming projects, he "will be working again soon so they have had a few weeks to be together without any distractions."

The source said Styles wanted to give Wilde—celebrating her 37th birthday Mar. 10—an unofficial guide to his adopted city, showing her "some of his favorite spots." Including his London flat, renovated down to the pink front door, guitar-filled "man cave" and turquoise velvet chesterfield sofa. 

"They both enjoy a quiet life at home," the source said of the couple. "They cook, watch movies, play games and hang out with friends. They keep it simple and it works."

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Because, actually, the "Watermelon Sugar" pop star and the actress-filmmaker's list of similarities isn't all that short. 

They both maintain some version of a pescatarian or vegetarian diet, rely on Pilates and stretching to stay strong physically and meditate to remain mentally sharp. "It has changed my life," Styles recently told Vogue of this twice-a-day-habit, "but it's so subtle. It's helped me just be more present. I feel like I'm able to enjoy the things that are happening right in front of me."

And both he and Wilde know just how challenging it can be to make a major life pivot. For Styles, it was being taken seriously as an actor, beating out scores of professionals to land his first role in the Oscar-nominated war opus Dunkirk not long after 1D's big split. "The good part was my character was a young soldier who didn't really know what he was doing," Styles reasoned to Vogue. "The scale of the movie was so big that I was a tiny piece of the puzzle. It was definitely humbling. I just loved being outside of my comfort zone."

It's a world Wilde knows well, having chosen an acting school in Dublin over four years at New York's Bard College, a decision that led to jobs on The O.C. and House

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"I have been an actress since I was a teenager and now I'm 35 and I'm really leaning into a new career of directing full-time," she told CNBC Make It in 2019 of her second act. "I think sometimes we all get into the mindset that if you've chosen your career at 25—that's it. You can't shift your career focus and it's just not true."

Ultimately it was a shared willingness to transform that brought the two together, Wilde recalling Styles' deft Dunkirk performance (she told Vogue it "blew me away—the openness and commitment") when she needed to replace Shia LaBeouf in her latest project. He, in turn, was impressed by her directorial debut, 2019's Booksmart, and was "very honored" to be cast in her second feature film.

Cue: Much screaming and an all-out "victory dance" with Oscar-nominated costume designer Arianne Phillips when he officially signed on because they knew the risk-taking, Met Gala-hosting, Gucci-collaborating Styles "has a real appreciation for fashion and style," Wilde explained to Vogue. "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."

Styles, though, is very opinionated when it comes to fashion, believing his appreciation dates back to the time he was cast as a church mouse in a school production. "I remember it was crazy to me that I was wearing a pair of tights," he told the fashion mag. "And that was maybe where it all kicked off!" 

Now, he continued, "I think if you get something that you feel amazing in, it's like a superhero outfit. Clothes are there to have fun with and experiment with and play with. What's really exciting is that all of these lines are just kind of crumbling away. When you take away 'There's clothes for men and there's clothes for women,' once you remove any barriers, obviously you open up the arena in which you can play. I'll go in shops sometimes, and I just find myself looking at the women's clothes thinking they're amazing."

Dimitrios Kambouris/Getty Images for The Met Museum/Vogue

And to Wilde, that's an extremely good look. 

"He's very modern," she extolled to Vogue of her star, who chose a Gucci jacket-and-dress combo for his cover shoot, "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."

So, yeah, not all that surprising how easily the two connected on set. 

"Harry is the sweetest, kindest guy—he's very charming," the source told E! News. "He was very supportive of her directing the movie. They were able to bounce ideas off of each other and share everything. He thinks she's incredibly talented and admires her."

Erik Pendzich/Shutterstock

Having gleaned a few lessons from Alain de Botton's The Course of Love, telling Vogue the 2016 book taught him that "when it comes to relationships, you just expect yourself to be good at it...[but] being in a real relationship with someone is a skill," Styles seems ready to apply his studies. 

Following a series of star-studded, but ultimately brief romances, he told Howard Stern last year that he'd like to find the person who inspires him to get down on one knee. Though he reasoned that part of that success would depend on his ability to keep a romance burning while in the public eye. 

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Harry Styles' Star-Studded Dating History

"It's always kind of a balance thing, because you want to date normally but then, you also want to protect it so it can be normal," he explained. "I think a big part of it is like, you wanna be able to spend enough time with each other where you can get to know each other before you have to deal with the extra stuff."

Several months in, it would appear he and Wilde, wed to filmmaker Tao Ruspoli before meeting Sudeikis in 2011, have worked out the kinks. "They have an incredible bond and are both very proud of each other's work," said the source. "They have fallen hard for each other."

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