Olivia Wilde & Harry Styles Are Reportedly “Taking A Break” After Almost 2 Years

The couple has kept their relationship low-key, but it’s still been filled with controversies and criticism.

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Olivia Wilde & Harry Styles' Relationship Timeline Started With 'Don’t Worry Darling'
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Harry Styles and Olivia Wilde may be going their separate ways. The pair, who first met in 2020 while filming Wilde’s second feature as director, Don’t Worry Darling, is “taking a break,” People exclusively reported on Nov. 18. "He's still touring and is now going abroad. She is focusing on her kids and her work in L.A.," the outlet revealed. "It's a very amicable decision." The magazine also noted that the public pressures of their relationship had been difficult. Bustle reached out to Harry Styles and Olivia Wilde for comment and did not hear back at the time of publication.

The actor and filmmaker broke the Internet in January 2021 when they were seen holding hands at the wedding of Styles’ agent before production on the film had wrapped, and they were confirmed to be an item just days later. Since then, Styles and Wilde rarely comment on their relationship but have proven to be going strong in more low-key ways, with the House star often showing up at Styles’ concerts.

Some fans speculated that the couple had split after nearly two years of dating when they walked the red carpet separately at the premiere of their new film Don’t Worry Darling, even standing apart in cast photos. However, The Sun denied those rumors and described them as “nonsense,” meaning that the couple likely chose to keep the focus on their film by minimizing their romance in public. After all, their relationship timeline proves that both Styles and Wilde like to keep their romance as private as possible.

September 2020: Harry Is Cast In Olivia’s Movie

On Sept. 20, Deadline revealed that Styles would replace Shia LaBeouf in Wilde’s second film as director, Don’t Worry Darling, joining lead actor Florence Pugh. Wilde confirmed the announcement on Instagram by sharing a side-by-side photo of the new co-stars and revealings their characters’ names in the caption. “Jack and Alice,” she wrote. “Very proud to work with these fine folks.”

November 2020: Olivia Splits From Jason Sudeikis & Praises Styles

On Nov. 14, 2020, it was announced that Wilde had split from ex-fiancé Jason Sudeikis after nearly nine years of dating and a seven-year engagement. PEOPLE reported that they separated at “the beginning of the year” and have stayed amicable for the sake of their 6-year-old son Otis and 4-year-old daughter Daisy. “It's been amicable and they’ve transitioned into a great co-parenting routine,” a source told the outlet. “The children are the priority and the heart of the family’s relationship.”

Earlier that month, Wilde spoke about Styles in his Vogue cover story, sharing that she did a “little victory dance” after learning that he had signed onto Don’t Worry Darling. “We knew that he has a real appreciation for fashion and style, and this movie is incredibly stylistic,” she explained. “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.”

The director went on to praise Styles’ confidence and lack of boundaries when it comes to fashion. “To me, he’s very modern, 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,” she said.

January 2021: Harry & Olivia Hold Hands At His Friend’s Wedding

Just four days into 2021, Wilde and Styles sent shockwaves across the internet when they were spotted holding hands while attending his agent's wedding. At the time, PEOPLE confirmed that they were an item, saying the new couple had been dating for a few weeks. “They were in Montecito, California this weekend for a wedding,” a source said. “They were affectionate around their friends, held hands and looked very happy.” US Weekly reported that Styles called Wilde his “girlfriend” in his wedding reception speech, all but making it official.

Entertainment Tonight gave more insight into how Wilde and Styles’ relationship blossomed into romance, reporting that they connected on the set of their film. “Olivia and Harry are together for long days on set and have gotten to know each other really well, so it's all very organic,” a source said, adding that Wilde “wouldn’t let a romantic relationship get in the way of a professional one, so anything they're doing is being done thoughtfully.”

February 2021: Olivia Praises Harry’s Work

As production on Don’t Worry Darling wrapped after months of delays, Wilde took to Instagram to pay tribute to Styles, praising his behavior on set and saying he was one of the few male actors that were willing to play a supporting role in a female-led film. “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 explained. “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.”

March 2021: Olivia Celebrates Harry’s Grammy

After Styles won his first Grammy Award on March 14, taking home Best Pop Solo Performance for his hit song “Watermelon Sugar,” Wilde subtly supported him on her Instagram Story by comparing him to his idols. First, she posted a photo of Rolling Stones frontman Mick Jagger performing in a leather jacket, feather boa, and... that’s about it, calling her boyfriend’s Grammys performance to mind. After, she shared a photo of Paul McCartney eating a slice of watermelon, which couldn’t be a more obvious nod to his Grammy-winning single.

July 2021: Harry & Olivia Make Out In Italy

While they may have kept their romance low-key, the couple proved they were still going strong with some classic PDA. After he wrapped filming My Policeman in London, Styles and Wilde took an Italian vacation and were seen dancing, cuddling, and making out on a yacht off the coast of Monte Argentario.

Dec. 2021: Olivia Is “Happier Than I’ve Ever Been”

In her December 2021 Vogue cover story, Wilde opened up about her relationship with Styles for the first time, albeit indirectly, addressing the public scrutiny of their 10-year age gap. “It’s obviously really tempting to correct a false narrative,” she said. “But 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.” The actor added that she’s “happier than I’ve ever been, and I’m healthier than I’ve ever been,” which just about says it all.

May 2022: Harry Talks Being Directed By Olivia

In a revealing SiriusXM interview, host Howard Stern asked Styles about falling in love on a movie set. “Oh, wow, how to answer this question?” he replied, before choosing to open up about working with Wilde on set rather than dive into their relationship. “I had a wonderful experience being directed by Olivia,” he said. “Acting is very uncomfortable at times. I think you have to trust a lot. 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.”

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August 2022: Olivia Speaks About Harry’s Fans

In Styles’ August 2022 cover story for Rolling Stone, Wilde commented on the negativity she has received from parts of the singer’s fervent fanbase, describing the majority of his fans as “deeply loving people” who don’t mock or criticize her. “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,” she told the outlet. “I don’t personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness.”

In the interview, Styles explained why he rarely speaks about his love life. “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.” Wilde echoed this sentiment in a separate interview with Variety later that month, explaining that both of them “go out of our way to protect” their relationship. “I'm not going to say anything about it because I've never seen a relationship benefit from being dragged into the public arena,” she said.

September 2022: Olivia Recalls Casting Harry

Wilde and Styles made their red carpet debut at the controversial Don’t Worry Darling premiere at Venice Film Festival on Sept. 4 — except they didn’t walk together. The couple seemingly chose to keep the focus on their film and stood away from each other in group photos with the cast.

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In her Vanity Fair cover story published a few days later, Wilde opened up about her decision to cast Styles in the film, explaining that his “non-actor” background was actually beneficial to her. “My thing with Harry was that I knew he was fearless,” she said. “I’d rather work with a non-actor who’s fearless than a trained actor who is full of hang-ups and baggage and judgment. What I love about working with singers and dancers is they commit 100 percent because, as a dancer, if you don’t commit 100 percent, you get hurt. With singers, it’s the same. If they sing at 30 percent, that song doesn’t work. I think actors sometimes think they can get away with 30 percent.”

For the first time, Wilde also disputed the theory that her relationship with Styles overlapped with her split from Sudeikis, who previously claimed that they had broken up. “The complete horsesh*t idea that I left Jason for Harry is completely inaccurate,” she said. “Our relationship was over long before I met Harry. Like any relationship that ends, it doesn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic. We were raising two kids during lockdown, so we co-parented through that time.”

October 2022: Wilde Takes Her “Special Salad Dressing” To Styles

A former nanny who was employed by Wilde and Sudeikis shared new details about their breakup with Daily Mail, claiming that Sudeikis was particularly upset about his ex sharing her “special” salad dressing with Styles. In text messages and stories shared with the website, Sudeikis is apparently incredulous that Wilde made the salad with her dressing in the family’s kitchen before leaving with it, presumably on her way to meet Styles. Sudeikis then reportedly lay under her car trying to prevent her from leaving. “Jason told me: ‘She made this salad and she made her special dressing and she's leaving with her salad to have dinner with [Harry],’” the nanny recounted. Bustle has reached out to Jason Sudeikis and Olivia Wilde for comment and has not heard back at the time of publication.

Some have since speculated that the dressing is the same recipe she shared when appearing on the 2020 Food Network special Questlove’s Potluck, which included red wine vinegar, Dijon mustard, honey, garlic, and olive oil.

Elsewhere in the interview, the former employee also revealed that Sudeikis allegedly found out about the affair via text messages on Wilde’s Apple Watch in November 2021. The estranged couple issued a joint statement to Daily Mail, denying the nanny’s reports. “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly,” the statement began. “Her now 18 month long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex. 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.”

November 2022: “Taking a Break”

People reported that the singer and actor are “taking a break” after almost 2 years together. “The public pressure on them has been difficult,” a source revealed to the magazine. “They've had ups and downs throughout the relationship.”

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