All the Signs Harry Styles and Olivia Wilde Were Heading for a "Golden" Romance

Lindsay Weinberg
·6 min read

2021 has already started off on a watermelon sugar high, after news broke on Monday, Jan. 4, that Harry Styles and Olivia Wilde are dating!

The artsy pair held hands while attending the weekend wedding of Harry's manager Jeff Azoff in Montecito, Calif. A source told E! News that Olivia and Harry were acting "couple-y" at the celebration and stayed in the same hotel room for the night. "They shared a room and did everything together," the source said. "They had a great time and are very happy."

Though it may come as a surprise that the former One Directioner, 26, and Booksmart director, 36, are now a thing, there have been plenty of signs hinting at their chemistry.

In fact, the couple has been spending time together for weeks while filming their horror movie Don't Worry Darling, which is directed by Olivia and stars Harry, alongside actors Florence Pugh, Chris Pine and Gemma Chan.

Harry Styles' Star-Studded Dating History

E! News has learned that production is starting up again this week in Los Angeles, and right now, the cast and crew are being tested for COVID-19. The production was previously halted in November due to a positive test on set.

As they prepare to shoot more scenes, E! News rounded up all the signs Harry was ready to say, "I live for you, I long for you, Olivia."

Olivia Wilde, Harry Styles
Olivia Wilde, Harry Styles

They Stayed at a House Together While Filming

While Don't Worry Darling was filming in Palm Springs, Calif. this year, a lot of the cast and crew stayed at a hotel. However, a source tells E! news that Olivia and Harry opted to instead live in a house together, away from the rest of the production team. They were in Palm Springs for a few weeks before returning to LA.

Harry and Olivia Were "Flirty" On Set

One big sign of the times was the off-screen chemistry between the stars. An insider tells E! News there were times Harry and Olivia seemed a bit "flirty" on set. He was even spotted visiting her trailer on Nov. 3.

Still, they kept it professional as the source noted it was "nothing over the top."

Olivia Wilde, Jason Sudeikis
Olivia Wilde, Jason Sudeikis

Olivia Is Newly Single

Very relevant: News just broke in November that the actress was separating from her partner of 10 years, Jason Sudeikis. The two share kids Otis, 6, and Daisy, 4, who remain their "priority" after the breakup.

Interestingly, People reported that Jason and Olivia actually broke it off several months prior, leaving plenty of time to move on. "It's been amicable and they've transitioned into a great co-parenting routine. The children are the priority and the heart of the family's relationship," a source told People.

But don't worry, darling: Jason and Olivia are still on good terms, as they were photographed hugging in Los Angeles about a week after multiple outlets revealed their split.

Olivia Has Been Very Public About her Praise for The Singer Turned Actor

Harry, whose other big acting credit was the World War II movie Dunkirk, immediately caught Olivia's eye when she was trying to replace Shia LaBeouf in her thriller. The mom of two told Vogue in November that the "Fine Line" artist "blew me away—the openness and commitment."

Olivia Wilde, Harry Styles
Olivia Wilde, Harry Styles

She also admitted that she and costume designer Arianne Phillips "did a little victory dance" when they heard they officially "had" Harry in the film. Olivia said, "We 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."

As if that wasn't enough, the House alum went on to call Harry a "modern" man. "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," she added. "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."

She Defended His Controversial Vogue Outfit

The 36 year old joined the chorus of celebs who stood up for Harry's history-making Vogue cover shoot, for which he was photographed wearing a Gucci jacket over a dress. After he appeared as the first solo male cover star, Olivia fiercely called one commentator "pathetic" for criticizing his bold fashion choice. Zach Braff, Jameela Jamil and Kathy Griffin also supported the stylish musician.

Harry Styles, Florence Pugh, Don't Worry Darling
Harry Styles, Florence Pugh, Don't Worry Darling

Harry Has Returned the Compliments, Too

The "Adore You" singer may have hinted that he adores Olivia in his recent Vogue cover story, as well. He said he loved Booksmart and was "very honored" to be a part of her second film, which Harry described as "a 1950s utopia in the California desert."

He Has a History of Dating Women Older Than He Is

Though the pair have a 10-year age difference, Harry's fans know that it's not out of the ordinary for the Brit. In 2011, he dated the late Love Island host Caroline Flack, who was 15 years his senior. She wrote in her book, "At the beginning it was all very playful. He joked about being attracted to older women." Plus, he was reportedly linked to Nicole Scherzinger of the Pussycat Dolls when he was 19 and she was 35 years old.

Among his other exes are Kimberly Stewart, 41, Erin Foster, 38, and Taylor Swift, 31.

Harry Left Miley on Read

Remember all the way back to last week when Miley Cyrus decided to shoot her shot with Harry? She revealed on the radio network Heart that she would rather kiss the boy bander over Justin Bieber. "Harry, that's easy," the "Malibu" singer said when asked. "And we have very similar tastes... I think sharing a closet, sharing a life together—it just makes sense."

However, we never heard a response from Harry. Could his new relationship explain his silence?

One Direction, SNL 2012
One Direction, SNL 2012

He Literally Has a Song Called "Olivia"

Okay, we're not going to call One Direction clairvoyant, but you have to admit it's extremely coincidental his band released the banger "Olivia" in 2015. On the track, the guys sing, "I've been idolizing the light in your eyes, Olivia" and "Don't let me go." Six years later... it's really happening!

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