Pop Culture
Olivia Wilde and Harry Styles’ Relationship Timeline: The Way They Were
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From coworkers to so much more! Olivia Wilde and Harry Styles took fans by surprise with their whirlwind romance, which began when they met on the set of Don’t Worry Darling.
The duo made headlines when they were photographed holding hands at Styles’ manager’s wedding in January 2021. A source exclusively told Us Weekly at the time that the twosome sparked a connection when they started working together.
“Harry and Olivia had chemistry almost instantaneously on set,” the insider said. “It was only a matter of time before they got together.”
Wilde’s romance with the British singer came two months after she split from fiancé Jason Sudeikis and three months after Styles joined her film. Sudeikis and the Booksmart director, who were together for over a decade, share two children: son Otis and daughter Daisy.
When reports of the relationship first emerged, a source told Us that Styles was not the reason for the House alum’s split from the Ted Lasso star.
“Harry did not break up an engagement,” the source said.
Although Styles didn’t come inbetween Wilde and Sudeikis, the new couple still tried to keep their relationship quiet on set in the beginning.
“Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” an insider told Us in January 2021. “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”
The psychological thriller, which revolves around a housewife in the 1950s, also stars Florence Pugh, Chris Pine, Gemma Chan, KiKi Layne and Nick Kroll.
After filming wrapped in February 2021, Wilde joined Styles in London, where they enjoyed some time to themselves.
“People tend to respect people’s privacy in London, so they probably feel comfortable walking around by themselves and don’t feel like they need a bodyguard,” an insider told Us in April 2021.
The duo were “spotted at local pubs” during their London getaway.
“They were walking close to each other and had their arms linked together,” added an insider, who bumped into the duo on one of their casual strolls. “They seemed very couply and cuddly with one another.”
The couple’s romance continued to heat up, with the Life Itself actress openly supporting her beau’s music and film careers. She “obviously” watched his Eternals appearance, which she noted via an Instagram comment, and even danced — along with her kids and his mother, Anne, — at various “Love on Tour” concerts.
“Olivia was nonstop dancing on the floor at Harry’s show at Madison Square Garden,” an eyewitness exclusively told Us of Wilde’s attendance at the musician’s October 2021 tour stop in New York City.
Scroll down to relive Styles and Wilde’s unexpected romance:
From coworkers to so much more! Olivia Wilde and Harry Styles took fans by surprise with their whirlwind romance, which began when they met on the set of Don’t Worry Darling.
The duo made headlines when they were photographed holding hands at Styles’ manager’s wedding in January 2021. A source exclusively told Us Weekly at the time that the twosome sparked a connection when they started working together.
“Harry and Olivia had chemistry almost instantaneously on set,” the insider said. “It was only a matter of time before they got together.”
Wilde’s romance with the British singer came two months after she split from fiancé Jason Sudeikis and three months after Styles joined her film. Sudeikis and the Booksmart director, who were together for over a decade, share two children: son Otis and daughter Daisy.
When reports of the relationship first emerged, a source told Us that Styles was not the reason for the House alum’s split from the Ted Lasso star.
“Harry did not break up an engagement,” the source said.
Although Styles didn’t come inbetween Wilde and Sudeikis, the new couple still tried to keep their relationship quiet on set in the beginning.
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“Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” an insider told Us in January 2021. “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”
The psychological thriller, which revolves around a housewife in the 1950s, also stars Florence Pugh, Chris Pine, Gemma Chan, KiKi Layne and Nick Kroll.
After filming wrapped in February 2021, Wilde joined Styles in London, where they enjoyed some time to themselves.
“People tend to respect people’s privacy in London, so they probably feel comfortable walking around by themselves and don’t feel like they need a bodyguard,” an insider told Us in April 2021.
The duo were “spotted at local pubs” during their London getaway.
“They were walking close to each other and had their arms linked together,” added an insider, who bumped into the duo on one of their casual strolls. “They seemed very couply and cuddly with one another.”
The couple’s romance continued to heat up, with the Life Itself actress openly supporting her beau’s music and film careers. She “obviously” watched his Eternals appearance, which she noted via an Instagram comment, and even danced — along with her kids and his mother, Anne, — at various “Love on Tour” concerts.
“Olivia was nonstop dancing on the floor at Harry’s show at Madison Square Garden,” an eyewitness exclusively told Us of Wilde’s attendance at the musician’s October 2021 tour stop in New York City.
Scroll down to relive Styles and Wilde’s unexpected romance:
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Credit: David Buchan/Shutterstock; David Fisher/BAFTA/Shutterstock; Charles Sykes/Invision/AP/Shutterstock
September 2020
Styles was cast in Don’t Worry Darling as Pugh’s husband. The musician replaced Shia LaBeouf, who was fired from the role by Wilde for reportedly clashing with the cast and crew.
Credit: Charles Sykes/Invision/AP/Shutterstock; Richard Shotwell/Invision/AP/Shutterstock
January 2021
The duo were spotted holding hands when they attended Styles’ manager Jeffrey Azoff’s nuptials in California together.
A source told Us that the former One Direction member even referred to Wilde as his “girlfriend” during his wedding speech.
Credit: PA Images/INSTARimages.com; JOHN NACION/startraksphoto.com
January 2021
Styles and Wilde continued to show off their new romance during a stroll in Santa Barbara, California. Photos published in January 2021 showed the actor reaching out to caress Wilde’s waist as they walked side by side.
Credit: Courtesy of Asif Ali/Instagram
February 2021
As filming for Don’t Worry Darling started to wrap, the New York native took to social media to celebrate her cast.
“Little known fact: most male actors don’t want to play supporting roles in female-led films,” Wilde wrote via Instagram in February 2021. “The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. 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.”
She continued: “Enter: @harrystyles, our ‘Jack.’ 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. 👊 #dontworrydarling.”
The couple also posed next to one another in a cast photo.
Credit: Erik Pendzich/Shutterstock; Jay L Clendenin/Los Angeles Times/Shutterstock
March 2021
The filmmaker subtly celebrated her beau after his Best Pop Solo Performance win at the 2021 Grammys.
Wilde posted a Polaroid-style photo of Paul McCartney taking a big bite out of a watermelon slice, hinting at Styles’ song “Watermelon Sugar.” Wilde captioned the Instagram post with a raised-hands emoji.
Credit: Anthony Harvey/Shutterstock; JM Enternational/Shutterstock
April 2021
“Harry and Olivia have been spending time in London,” a source exclusively told Us. “She’s been staying at his place. They’re trying to be as low key as possible and go to places that aren’t too crowded.”
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May 2021
Styles was cast alongside Emma Corrin in My Policeman — and PDA-filled pics from set sent fans into a frenzy. However, an insider told Us that Wilde didn’t mind at all.
“[Olivia’s] not bothered by Harry’s on-camera romance with Emma. This isn’t the first time she’s been in a relationship and had to deal with her partner kissing other actresses,” the source shared in May 2021. “If anything, she’s excited about his role in the film and thinks he’s doing an amazing job. Plus, she’s confident in their relationship as they’re going very strong!”
Credit: ROGER WONG/INSTARimages.com; Jean-Marc HAEDRICH/SIPA/Shutterstock
July 2021
“Olivia’s really smitten by Harry,” an insider exclusively told Us after the couple were spotted packing on the PDA on vacation in Italy. “He makes her really happy. It’s like he’s brought out this giddy side of her. The thing that works for them is that they don’t hide their relationship from the public. They don’t care who’s around watching them pack on the PDA.”
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July 2021
“Olivia and Harry have an ease to their relationship, they love and support each other, but also let each other be free and work on their own,” a source told Us about the duo’s strong connection.
The insider also noted that Wilde and Styles have been in “constant communication when they’re not together” amid separate professional projects.
“Both of them respect the other’s work and never want to get in the way of each other,” the source added.
Credit: Chelsea Lauren/Shutterstock; MEGA
September 2021
Wilde was spotted at Styles’ concert in Las Vegas on September 4, filming and dancing along to her boyfriend’s music.
Credit: Matt Baron/Shutterstock
December 2021
The director was spotted running errands in Los Angeles on December 5 wearing a black sweatshirt from Styles’ cosmetic business. The hoodie displayed the “Pleasing” logo across the chest.
Credit: Courtesy of Gemma Chan/Instagram
January 2022
“Watching now obviously 🙌🙌🙌,” Wilde wrote via Instagram comment after Styles’ Eternals costar Gemma Chan shared behind-the-scenes pictures of herself and the singer in their MCU superhero costumes.
Credit: Beretta/Sims/Shutterstock; Rob Latour/Shutterstock
April 2022
After Styles dropped the first single from his third album, “As It Was,” fans were quick to parse through the lyrics for clues. Some listeners were convinced the bridge hinted at his romance with Wilde with the line, “Leave America, two kids follow her,” which fans believed was a reference to Otis and Daisy.
While discussing the inspiration behind the track, Styles gushed to SiriusXM’s The Morning Mash Up that he felt “really happy at the moment,” which had a positive effect on his songwriting. “I feel like it’s the first time I feel like I’m kind of making music and putting music out from a real place of kind of personal freedom,” he said.
Credit: Image Press Agency/NurPhoto/Shutterstock; HS/MEGA
April 2022
Eagle-eyed fans spotted Wilde walking through the Coachella crowds shortly before Styles took the stage on April 15. During his headlining performance, the rockstar performed several of his most popular hits, two unreleased songs and a surprise duet with Shania Twain.
Credit: Beretta/Sims/Shutterstock; Rob Latour/Shutterstock
May 2022
The couple were spotted strolling in Italy ahead of the release of Styles’ third album, Harry’s House. “Olivia and Harry love going to Italy together,” an insider told Us of the duo’s vacation. “It’s their favorite place to unwind and reconnect as a couple. They both love the food, the people, the architecture, everything. They are excited to spend a lot of quality time together before he leaves to go back on tour.”
Credit: Kristina Bumphrey/StarPix/Shutterstock; Gregory Pace/Shutterstock
May 2022
“I had a wonderful experience being directed by Olivia,” Styles explained during an appearance on SiriusXM’s The Howard Stern Show. “Acting is kind of uncomfortable at times. You have to trust a lot. Being able to trust your director is a gift, that was very helpful.
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May 2022
“🙌,” Wilde captioned an Instagram Story clip of a scene from 2018’s Cold War, which she set to Styles’ “Music for a Sushi Restaurant.” (The song was released on his Harry’s House album on May 20, 2022.)
Credit: Shutterstock (2)
May 2022
Despite being separated by their respective work obligations, a source told Us that Wilde and Styles were still going strong. “They’re not nervous about spending time apart, it adds to the attraction when they reunite after some time off,” the insider revealed. “Both of them are secure and positive about what the future holds for them.”
The couple have also worked out ways to make sure they spend time together, even when the “As It Was” singer heads out on tour. “Harry’s excited about his tour but bummed it’ll take him away from Olivia for a while,” the source added. “But she’ll come to a few of the gigs and they’re planning on making fun little trips in various cities when she can take a break herself.”
Credit: Erik Pendzich/Shutterstock
June 2022
During an appearance on the “Spout” podcast, Styles was asked to explain the Harry’s House track “Cinema,” which deals with the feeling of not being “cool” enough for your partner — and the song many fans believe is about Wilde.
“We are all human,” the singer responded when the host claimed they couldn’t imagine anyone would be “too cool” for someone like Styles. “I think it’s, like, when you like someone, that initial phase. Am I doing things right? Before you get comfortable with each other and it’s kinda, like, all of that stuff happens at the start of something,” he said, seemingly referring to his current relationship with Wilde.
The episode went on to replay part of Styles’ May 2022 interview with Stern, in which the “Golden” artist was asked to discuss what it was like to “fall in love” on a movie set. “I had a wonderful experience being directed by Olivia,” Styles cautiously shared. “Being able to trust your director is a gift.”
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August 2022
Sudeikis publicly served Wilde with custody paperwork in April 2022 during her CinemaCon appearance as the director promoted her film Don’t Worry Darling, which stars Styles.
While an insider told Us at the time that Sudeikis “would never condone” Wilde being served in “such an inappropriate manner,” he also did not want her to be served in front of their children or at Styles’ residence.
“I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present,” Sudeikis wrote in his paperwork, which the Daily Mail obtained in August. “I did not want service to take place at the children’s school because parents might be present.”
Wilde has since filed her own custody petition, alleging that Sudeikis’ legal tactics were “outrageous” and meant to publicly embarrass her.
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August 2022
One day after they were spotted strolling in lower Manhattan, the couple were photographed leaving NYC’s Rubirosa restaurant after having dinner. The pair both dressed casually for the evening, with the “Daylight” crooner opting for a crocheted, deep V-neck blouse with trousers and the actress wearing a toile-patterned maxi skirt with sneakers and a T-shirt.
Credit: Kristin Callahan/ACE Pictures/Shutterstock; Charles Sykes/Invision/AP/Shutterstock
August 2022
The pair made rare remarks about their relationship in Styles’ September 2022 Rolling Stone cover story. “What I don’t understand about the cruelty you’re referencing is that that kind of toxic negativity is the antithesis of Harry, and everything he puts out there,” Wilde said of dealing with online hate. “I don’t personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness.”
Styles, for his part, explained why he prefers to keep his personal life under wraps. “I’ve never talked about my life away from work publicly and found that it’s benefited me positively,” he said. “There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way.”
Credit: Beretta/Sims/Shutterstock; Mark Von Holden/Invision/AP/Shutterstock
August 2022
When asked about her relationship with her Don’t Worry Darling costar, Wilde told Variety, “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.”
The filmmaker also opened up about the heightened scrutiny she’s faced since splitting from Sudeikis. “The last two years, my family has gone through this kind of restructuring and a revolution that should be a totally personal experience,” she said. “And it’s not. The most painful element of it has been women shaming me for making a decision that was for my own health and happiness. … When people see me not with my kids, it’s always, ‘How dare she.’ I’ve never seen anyone say that about a guy. And if he is with his kid, he’s a f–king hero.”
Credit: Shutterstock
September 2022
Wilde has been a staple at many of Styles’ Love on Tour concerts. “[Opening act Jenny Lewis] was looking around, and she said, ‘That’s a lot of happy women,’” Wilde recalled to Vanity Fair. “I instantly started crying. Where else do we see this? Happy women? Women brought together with joy, loving each other, and cheering for each other? This has been like a gift to be amongst this.”
She added: “His fans are a beautiful and loving group of people. I have had the opportunity to witness some of the most moving examples of compassion and acceptance [while] standing in a room with 20,000 happy women [and men].”
Credit: Splash
September 2022
After sitting on opposite ends of the room at a screening event for Don’t Worry Darling, the duo attended an afterparty for the film’s New York City premiere at The Bowery Hotel. Styles wore pinstriped pants with a double-breasted jacket, while Wilde opted for head-to-toe black.
Credit: Matt Baron/Shutterstock
October 2022
A former nanny of Wilde and Sudeikis’ children alleged to the Daily Mail that not only had the director cheated on her fiancé with the “Matilda” singer, but that the Ted Lasso star once laid underneath her car to stop her from visiting Styles.
The caregiver also claimed that Sudeikis was devastated when Wilde made her “special” salad dressing for the performer. The former couple, for their part, slammed the nanny’s allegations in a rare, joint statement shared with Us.
“As parents, it’s incredibly upsetting to learn that a former nanny of our two young children would choose to make up such false and scurrilous accusations about us publicly,” Wilde and Sudeikis told Us. “This is the unfortunate apex of a now, 18-month-long campaign of harassing us, as well as our loved ones, close friends and colleagues. We will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone.”
Credit: Angel Marchini/SOPA Images/Shutterstock; John Nacion/NurPhoto/Shutterstock
October 2022
Days after Wilde denied her former nanny’s allegations, the actress was spotted attending a Wolf Alice concert with Styles in Los Angeles. Videos taken by concert attendees showed the duo standing next to each other in the venue, though they seemingly kept PDA to a minimum.
Credit: Richard Young/Shutterstock; Jordan Strauss/Invision/AP/Shutterstock
November 2022
Us confirmed that the twosome called it quits after nearly two years of dating.
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December 2022
“Olivia is still very much upset about the breakup, but is trying to move on,” a source exclusively told Us, noting that the actress’ December girls trip was a way for her to “decompress” after the split. “Olivia has been leaning on friends.”
While Wilde has been trying to get out post-split, “dating isn’t on her list of priorities,” the insider added.
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Yana Grebenyuk
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