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- Olivia Wilde's Custody Battle With Jason Sudeikis Put A Strain On Her Relationship With Harry Styles
From coworkers to lovers to former lovers, Olivia Wilde and Harry Styles shocked fans with their whirlwind romance when they met on the set of Wilde's now-controversial movie Don’t Worry Darling back in September 2020. The pair sparked headlines when they first stepped out as a couple and were photographed holding hands at Harry Styles' manager's wedding in January 2021.
Filmmaker Olivia Wilde's relationship with British singer Harry Styles was rooted in controversy from the very beginning of their romance, which began just two months after she broke off her engagement to longtime fiancé and father to her two children, Jason Sudeikis.
Although Wilde and Styles consistently remained tight-lipped about their relationship to the press, it was the cause of major drama surrounding the filming of Don't Worry Darling, the psychological thriller directed by Olivia Wilde that went viral for the off-screen contention surrounding the former couple and co-star Florence Pugh.
While Harry Styles and Olivia Wilde have now split, their relationship seemed doomed from the very beginning, here's why there was something not quite right about their relationship from the start...
Jason Sudeikis Was "Really Hurt" by Olivia Wilde's Relationship With Harry Styles
Several outlets broke the news in November 2020 that Wilde and Sudeikis had ended their engagement after 9 years together, with a source saying: "They adore each other and have nothing but the utmost respect for one another. They will continue to be each other’s biggest supporters, especially when it comes to parenting their children". The Source also revealed that the former couple moved out of their home in Brooklyn, New York at the end of 2019, adding that this was "the beginning of the end" of their relationship.
Olivia Wilde's relationship with "boy toy" Harry Styles was made public in January 2021 when the two were photographed holding hands at the wedding of Styles' manager, Jeffrey Azoff. TMZ reported that there were only 16 people present at the covid safe wedding, and Styles took Wilde as his plus one, the pair were seen holding hands throughout the event.
There was speculation surrounding the timing of the relationship, with many suggesting that it was suspicious. However, Olivia Wilde was quick to shut these rumors down in an interview with Variety, saying: "The complete horses--t idea that I left Jason for Harry is completely inaccurate. Our relationship was over long before I met Harry."
Olivia Wilde's newfound relationship with Harry Styles must have been the cause for contention between Wilde and Sudeikis, as the two were seen briefly reuniting at Sudeikis's LA home just hours after the photographs of Wilde and Styles were leaked to the press.
In January 2021, ET reported that the We're the Millers star was "really hurt" by Olivia Wilde's relationship with musician Harry Styles, with a source saying: "Sudeikis had hoped that him and Olivia Wilde would eventually reconcile and get back together. He has been really hurt and somewhat jealous that Olivia has moved on with Harry Styles".
The Drama Surrounding The Cast Of Don't Worry Darling Went Viral
The rumors surrounding the production of Don't Worry Darling prior to the movie's release in September 2022 seemed endless, with some eluding that Olivia Wilde and leading lady Florence Pugh didn't see eye to eye on set. Fans also noticed the awkwardness at the movie's premiere which took place at Venice Film Festival, with some cast members not speaking a word to each other. Florence and Olivia never posed together, and Florence Pugh was also notably absent from the movie's press call.
One rumor alleged that Harry Styles and Florence Pugh hooked up prior to his blossoming relationship with Olivia Wilde, which caused major tension on set. This rumor was later corroborated by Wilde and Sudeikis's ex-nanny Erika Genaro. In a video posted online, Genaro claimed that Sudeikis told her that “Flo was f–king Harry, and she had a boyfriend.” However, this was quickly shut down in a rare join statement released by Wilde and Sudeikis: "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."
Another rumor hinted that Florence Pugh was irate about Olivia Wilde allegedly cheating on Jason Sudeikis with Harry Styles. With a source telling Pagesix: “I can tell you for a fact that Flo seeing Olivia and Harry all over each other on set did not go down well, as Olivia was still with Jason when she first hooked up with Harry,” an insider told the publication. “Jason and the kids visited Olivia on set at the beginning a few times, so I think this all made people feel a little uncomfortable,” the source added.
However, the rumors were later shut down by people who worked on the film in a statement released to People that read: "As a crew, we've avoided addressing the absurd gossip surrounding the movie we're so proud of. Any allegations about unprofessional behavior on the set of Don't Worry Darling are completely false."
They then went on to call Olivia Wilde an 'incredible leader and director'.
Olivia Wilde's Custody Battle With Jason Sudeikis Put A Strain On Her Relationship With Harry Styles
While Wilde and Sudeikis were seemingly on good terms following their split, this changed in April 2022 when Olivia Wilde was served custody papers on stage at ComicCon. The director was introducing a new trailer for her movie Don't Worry Darling which starred her then-boyfriend Harry Styles, when an unknown person approached the stage and served her with custody papers.
A representative for Sudeikis told Variety that the dad of two had no idea that she would be served so publicly, saying: “Mr. Sudeikis had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved, and he would never condone her (Olivia Wilde) being served in such an inappropriate manner.”
In an August 24 interview with Variety, Olivia Wilde publicly addressed the events that unfolded at ComicCon which led to her being publicly served custody papers, saying: "It was my workplace. In any other workplace, it would be seen as an attack. It was really upsetting, it shouldn’t have been able to happen. There was a huge breach in security, which is really scary."
She also took a jab at her ex fiancé Sudeikis, saying: "I hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing. To try to sabotage that was really vicious... Sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship."
It was somewhat confirmed that Olivia Wilde's relationship with Harry Styles was causing strife in her co-parenting relationship with Jason Sudeikis when the pair were photographed hugging each other in January 2023, just months after her split from Harry Styles. A source told TMZ: "Olivia has been focusing all her energy on her kids and family since her split with Harry, and now that they're broken up, it's been easier for Jason and Olivia to get along."
Adding that: "Jason has been trying to be supportive of Olivia and a good co-parent during this transition. Things between Jason and Olivia are cordial and going well."
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