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Daily Mirror
Daily Mirror
Entertainment
Hana Carter

Where did it go wrong? Olivia Wilde and Jason Sudeiki's doomed nine year romance

Olivia Wilde was served custody papers by her ex Jason Sudeikis as she gave a live presentation on her new movie.

The humiliating gesture is the latest in the public breakdown of the couple, who share two children together.

Their nine year relationship broke down after Olivia cast her now-boyfriend Harry Styles in her upcoming film Don't Worry Darling.

Jason and Olivia met in 2011 at a Saturday Night Live wrap party when they were both recently single.

Olivia, 38, had just ended her eight-year marriage to filmmaker Tao Ruspoli while Jason had divorced screenwriter and actress Kay Cannon, who he married in 2004.

Speaking of his early crush on Olivia, The Horrible Bosses star told Stephen Colbert on The Late Late Show: "I actually came off looking a lot cooler than I really am."

The couple's split was said to be 'amicable' and that they were putting the children first (WireImage)

"I had heard through the grapevine, through mutual friends that weren't exactly her best girlfriends, that would report back, 'Oh, you know, I think she's dating someone,' so I didn't make any sort of moves.

"I was just very, very busy with other things."

Olivia agreed: "I was just learning to be by myself; I'd been divorced nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls**t."

It was confirmed that they were custody documents from Jason (AFP via Getty Images)

After six months the pair were engaged with Jason popping the question at Christmas in 2013.

Months later they welcomed their first child Otis and had a daughter Daisy two years later.

In 2016 Olivia told Net-a-Porter's Edit: "We are seriously connected," she said.

"Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it's like, 'Oh, we're committed and promised already."

As well as getting on well behind closed doors, Jason and Olivia proved to be winning on other levels as they signed up to work together.

When Olivia made her debut as a director in 2019 with her movie Booksmart, Jason made a cameo in the movie, while he was looking after their children.

Olivia and Harry were spotted holding hands (GC Images)

However, it all came crashing down in 2020 when Olivia was casting for her second film Don't Worry Darling.

The director, who has "a zero a**hole policy" gave the role of her leading man to former One Directioner Harry Styles.

Speaking to Vogue, Olivia said that she and the film's costume designer Arianne Phillips were excited to have him on set due to his love for gender fluid fashion.

"She [Arianne] and I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style," Olivia said.

"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."

But just hours after the article went to print in November, she and Jason split.

A source told PEOPLE magazine that the split was "amicable".

There was initial confusion over when Harry and Olivia started dating (Instagram)

"It's been amicable and they've transitioned into a great co-parenting routine.

"The children are the priority and the heart of the family's relationship."

"They just fell out of love in a romantic way, but still have love towards one another as people."

This was followed by conflicting reports of when the couple actually split, with some saying it was at the start of 2020, while others were saying it was the Autumn of that year.

Jason and Olivia met after they met at a wrap party (Getty Images)

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Rumours of Olivia and Harry's romance sparked in January 2021 after they were spotted holding hands at a wedding in Montecito, California.

A source continued: "She began filming [Don't Worry Darling] in September, and by October, he began to get the impression that she wanted out. By November, they'd announced their split."

"The source emphasized 'that's how quickly it happened,' adding that 'none of it happened until she began filming with Harry."

The director was in the middle of a presentation in Las Vegas for 4,100 industry experts at CinemaCon when she was handed the papers from Jason.

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