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

Mar. 15, 2025

01of 12His Biggest FanAnthony Pham/via GettyAs Harry Styles kicked off his Love on Tour show in Las Vegas in September 2021, Olivia Wilde wasseen in the crowd having a lot of fun, a concertgoer toldE! Newsat 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 Stylesin Los Angeles in mid-November.

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His Biggest Fan

Anthony Pham/via Getty

As Harry Styles kicked off his Love on Tour show in Las Vegas in September 2021, Olivia Wilde wasseen in the crowd having a lot of fun, a concertgoer toldE! Newsat 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 Stylesin Los Angeles in mid-November.

02of 12Very ‘Pleasing’BackgridWildewas an early supporter ofStyles’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.

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Very ‘Pleasing’

Backgrid

Wildewas an early supporter ofStyles’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.

03of 12Tour TeesOlivia Wilde wore a Love on Tour T-shirt.The Image DirectTheBooksmartdirector repped Styles while out grabbing Starbucks in L.A. in November 2021. She worehis’ 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 aftera fan spotted her at Styles' San Diego concertwith her kids Otis and Daisy.

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Tour Tees

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

TheBooksmartdirector repped Styles while out grabbing Starbucks in L.A. in November 2021. She worehis' 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 aftera fan spotted her at Styles' San Diego concertwith her kids Otis and Daisy.

04of 12Keep It KindTheImageDirectAnother 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.

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Keep It Kind

TheImageDirect

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.

05of 12Meeting the FamilyOlivia Wilde; Harry Styles.Steve Granitz/FilmMagic; Kevin Mazur/GettyThe 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-fiancéJason Sudeikis.

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Meeting the Family

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-fiancéJason Sudeikis.

06of 12Yours for EternityGemma Chan/InstagramGemma Chan shared behind-the-scenes photos of herself and Styles on the set ofEternalsin 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 filmDon’t Worry Darling.)In the comment section,Wilde reacted to the photosof her boyfriend and Chan, writing, “Watching now obviously 🙌🙌🙌.”

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Yours for Eternity

Gemma Chan/Instagram

Gemma Chan shared behind-the-scenes photos of herself and Styles on the set ofEternalsin 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 filmDon’t Worry Darling.)

In the comment section,Wilde reacted to the photosof her boyfriend and Chan, writing, “Watching now obviously 🙌🙌🙌.”

07of 12Pleased to RepostOlivia Wilde/InstagramThe 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 revealon her Instagram Story with the clever caption, “I find this very pleasing.”

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Pleased to Repost

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 revealon her Instagram Story with the clever caption, “I find this very pleasing.”

08of 12Special ShoutoutsAfter her movieDon’t Worry Darlingwrapped,the director posted tributes to the film’s actors and crewon 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.

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Special Shoutouts

After her movieDon’t Worry Darlingwrapped,the director posted tributes to the film’s actors and crewon 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.

09of 12A ‘Revelation’Rachel Murray/Getty; Dia Dipasupil/GettyThe director shared the first full trailer ofDon’t Worry Darlingexclusively 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.”

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A ‘Revelation’

Rachel Murray/Getty; Dia Dipasupil/Getty

The director shared the first full trailer ofDon’t Worry Darlingexclusively 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.”

10of 12’Happier Than Ever’Olivia Wilde; Harry Styles.John Shearer/Getty; Dia Dipasupil/FilmMagicWildebriefly spokeabout the spotlight on the couple’s relationship in a cover story forVogue’sJanuary 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.”

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‘Happier Than Ever’

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

Wildebriefly spokeabout the spotlight on the couple’s relationship in a cover story forVogue’sJanuary 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.”

11of 12Rolling in the DeepHarry Styles, Olivia Wilde.Kevin Mazur/WireImage, Stephen Lovekin/ShutterstockContinuing to keep chatter on their relationship to a minimum, Wilde toldVarietyshe wasn’t “going to say anything about” herrelationship"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 sentimentswithVanity 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.’ "

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Rolling in the Deep

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

Continuing to keep chatter on their relationship to a minimum, Wilde toldVarietyshe wasn’t “going to say anything about” herrelationship"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 sentimentswithVanity 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.’ "

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Movie Magic

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

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.

source: people.com