How Harry Styles and Olivia Wilde Supported Each Other Throughout Their Relationship

The pair quietly began dating in January 2021 after working together on the film Don't Worry Darling, and kept their courtship private despite public interest

01 of 12

His Biggest Fan

Harry Styles Performs At MGM Grand Garden Arena
Anthony Pham/via Getty

As Harry Styles kicked off his Love on Tour show in Las Vegas in September 2021, Olivia Wilde was seen in the crowd having a lot of fun, a concertgoer told E! News at the time.

"She was so happy and dancing all night!" the eyewitness told the outlet. "It was very cute. She was singing along to almost every song and having a good time with the people she was with."

Throughout the tour, Wilde was often spotted in crowds spanning the globe, most recently bringing her kids to see Styles in Los Angeles in mid-November.

02 of 12

Very 'Pleasing'

Olivia Wilde

Wilde was an early supporter of Styles' beauty brand Pleasing. The former One Direction star released his non-binary brand in November 2021 and in the weeks following, Wilde rocked Pleasing merch while out around town.

03 of 12

Tour Tees

Olivia Wilde
Olivia Wilde wore a Love on Tour T-shirt. The Image Direct

The Booksmart director repped Styles while out grabbing Starbucks in L.A. in November 2021. She wore his' Love on Tour concert merch: a short-sleeve, white tee shirt adorned with two black bunnies on the front, along with "Love On Tour" written across the chest in bright orange.

The snap was taken one day after a fan spotted her at Styles' San Diego concert with her kids Otis and Daisy.

04 of 12

Keep It Kind

Olivia Wilde

Another coffee run, another opportunity to rep Styles and his music. The star was seen out in L.A. in October 2021 wearing a black hoodie embossed with the words "Treat People with Kindness," which is the name of one of Styles' songs.

05 of 12

Meeting the Family

LOS ANGELES, CALIFORNIA - NOVEMBER 06: Olivia Wilde arrives at the 10th Annual LACMA ART+FILM GALA Presented By GucciLos Angeles County Museum of Art on November 06, 2021 in Los Angeles, California. (Photo by Steve Granitz/FilmMagic) LOS ANGELES, CALIFORNIA - MARCH 14: Harry Styles attends the 63rd Annual GRAMMY Awards at Los Angeles Convention Center on March 14, 2021 in Los Angeles, California. (Photo by Kevin Mazur/Getty Images for The Recording Academy ) Steve Granitz/FilmMagic; Kevin Mazur/Getty
Olivia Wilde; Harry Styles. Steve Granitz/FilmMagic; Kevin Mazur/Getty

The mom of two continued balancing her family, her relationship with Styles and work. Additionally, as the couple's relationship got more serious, Wilde introduced her little ones — son Otis and daughter Daisy — to Styles, a source told PEOPLE in December 2021.

"[They try] to see each other as much as possible," said the source. "Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour."

The insider added: "She always seems focused on just making it all work. She is really Harry's biggest fan."

The source also revealed that "Olivia is also spending time with Harry's mom."

Wilde shares Otis and Daisy with ex-fiancé Jason Sudeikis.

06 of 12

Yours for Eternity

Harry Styles Smiles Wearing His Eternals Costume in Throwback Photos Shared by Gemma Chan
Gemma Chan/Instagram

Gemma Chan shared behind-the-scenes photos of herself and Styles on the set of Eternals in January 2022. The fun photo set of the two featured them posing seriously in the first shot, and then smiling in the next. (The two also starred in Wilde's film Don't Worry Darling.)

In the comment section, Wilde reacted to the photos of her boyfriend and Chan, writing, "Watching now obviously 🙌🙌🙌."

07 of 12

Pleased to Repost

Olivia Wilde - Harry Styles
Olivia Wilde/Instagram

The first hint of Wilde and Styles' relationship to hit social media was when the singer first launched Pleasing with a Story on Instagram. Just hours later, the actress reposted the brand reveal on her Instagram Story with the clever caption, "I find this very pleasing."

08 of 12

Special Shoutouts

After her movie Don't Worry Darling wrapped, the director posted tributes to the film's actors and crew on Instagram — including one for the leading man in her film, Styles.

In the caption, Wilde explained how most male actors don't want to appear in female-led films and take the lesser role, which in turn makes those movies hard to finance. But Styles jumped in without reservation to play backup to Florence Pugh's leading role.

"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,' " Wilde wrote alongside a black-and-white shot of Styles sitting in a classic car.

"Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our 'Alice', but 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."

Styles joined the cast late after Wilde let Shia LaBeouf go from the leading role.

09 of 12

A 'Revelation'

Olivia Wilde and Harry Styles
Rachel Murray/Getty; Dia Dipasupil/Getty

The director shared the first full trailer of Don't Worry Darling exclusively with audiences at CinemaCon in Las Vegas in April, calling the project "ambitious" and saying that Styles' performance is "truly a revelation."

Wilde also teased the Grammy winner, referring to him as "an up-and-coming actor with no other career that I'm aware of."

10 of 12

'Happier Than Ever'

Olivia Wilde, Harry Styles
Olivia Wilde; Harry Styles. John Shearer/Getty; Dia Dipasupil/FilmMagic

Wilde briefly spoke about the spotlight on the couple's relationship in a cover story for Vogue's January 2022 issue.

"It's obviously really tempting to correct a false narrative," she told the outlet of the attention surrounding their romance. "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."

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

Styles shared similar sentiments in an interview with SiriusXM months later.

"I also feel really happy at the moment and I feel like it's the first time I feel like I'm making music and putting music out from a real place of personal freedom," he said. "And that is a really liberating place to [be] creating from and now putting it out."

11 of 12

Rolling in the Deep

Harry Styles, Olivia Wilde
Harry Styles, Olivia Wilde. Kevin Mazur/WireImage, Stephen Lovekin/Shutterstock

Continuing to keep chatter on their relationship to a minimum, Wilde told Variety she wasn't "going to say anything about" her relationship "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," she continued. "I think it's out of experience, but also just out of deep love."

She shared similar sentiments with Vanity Fair, adding, "I think once you crack open the window, you can't then be mad when mosquitoes come in. It's like, 'You opened the window.' "

12 of 12

Movie Magic

Gemma Chan, Harry Styles, Sydney Chandler, director Olivia Wilde, Chris Pine, Florence Pugh and Nick Kroll attend the "Don't Worry Darling" red carpet at the 79th Venice International Film Festival
From left: Gemma Chan, Harry Styles, Sydney Chandler, Olivia Wilde, Chris Pine, Florence Pugh and Nick Kroll at the Venice Film Festival Sept. 5, 2022. Vittorio Zunino Celotto/Getty Images

In an interview with Howard Stern for his SiriusXM show, Styles was asked point-blank by the shock jock, "You fell in love on a movie set?"

"Oh, wow, how to answer this question?" the actor and singer answered of his time filming Don't Worry Darling (cast pictured). "I had a wonderful experience being directed by Olivia. I think there is something that obviously ... acting is very uncomfortable at times. I think you have to trust a lot."

He also noted, "Being able to trust your director is a gift."

"That was very helpful, and it really meant for a really nice experience working on that movie," Styles said.

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