A brief (but fascinating) history of Olivia Wilde and Jason Sudeikis’ relationship

In an incredibly awkward scene, Olivia Wilde was interrupted on stage at CinemaCon this week to be served custody papers from her ex-fiance Jason Sudeikis.

Since the news broke, a spokesperson for Sudeikis’ claimed the actor has “no prior knowledge” of the details of the court document’s delivery and the inconvenient circumstances were a fault on the part of the process service company.

A source told Variety that, “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 being served in such an inappropriate manner.”

Either way, the events unfolded in a particularly uncomfortable and humiliating manner for Wilde, 38, who was in the midst of presenting the trailer for her second directorial endeavour, Don’t Worry Darling, at the film convention in Las Vegas. Wilde, dressed in a midnight blue Alberta Ferretti suit was midway through her sentence when she was interrupted by a staff member sliding a manila envelope labelled “personal and confidential” to her across the stage.

Taken aback, the Booksmart director broke off her speech to an audience of 4,000 film executives and asked: “This is for me?” Wilde was photographed briefly looking at the document before continuing seemingly unfazed with her presentation. At the time, onlookers relayed that Wilde assumed the envelope was a script written by someone in the audience. Before opening the document Wilde asked, confused, “Is this a script? Ok, got it. Thank you.”

Wilde and Sudeikis have two children together, eight-year-old son Otis and five-year-old daughter Daisy. The couple began dating in November 2011 after meeting at a Saturday Night Live wrap party before getting engaged in December 2012 and eventually splitting in November 2020. Two months later photos were published of Wilde holding hands with singer Harry Styles, 28, at his agent’s wedding in Montecito, California, in January 2021.

Styles and Wilde have never publicly confirmed their relationship, but they have been pictured together several times over the last year, including kissing on a yacht in ​​Monte Argentario, off the coast of Tuscany in July. Since then, Wilde has been pictured supporting the singer at Styles’ concerts, including his latest performance at Coachella in Palm Springs last week. A viral TikTok video seems to show Styles catching a glimpse of his Wilde from the stage, before bursting into a wide grin, while singing his hit song, “Sign of the Times.”

Despite coming under heavy, often sexist media scrutiny in the aftermath of her marriage split and new relationship with the One Direction singer, Wilde has kept a dignified silence on matters of her heart. The controversy erupted after People magazine and Us Weekly speculated about the timeline discrepancies between her marriage and new relationship with Styles, who she had cast as the male lead in Don’t Worry Darling three months before the end of her marriage.

In an interview with GQ, Sudeikis fanned the flames of the speculation by suggesting even he didn’t have total clarity about the end of his relationship. He told journalist Zach Baron: “I’ll have a better understanding of why in a year,” before adding, “and an even better one in two, and an even greater one in five, and it’ll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle.”

Meanwhile, Wilde refused to comment on the public scrutiny, telling American Vogue last year: “It’s obviously really tempting to correct a false narrative… 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.”

“In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us,” she says. But, she adds: “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.”

But Styles wasn’t the first option for the film. Shia LaBeouf was originally contracted to play the male protagonist opposite Florence Pugh. Set in the 1950s, the psychological thriller follows a housewife (Pugh) living in a utopian experimental community, attempting to wrestle with the reality of her marriage after uncovering a dark secret. Five months after being cast in the role, the production issued a statement saying that LaBeouf had had to pull out of the project due to a “scheduling conflict”, but it was reported later that the actor had been fired due to alleged poor behaviour.

A source close to the film told Variety that the actor had been “off-putting” to Wilde and the other crew members and the source added that Wilde “is known to build collaborative sets with a zero asshole policy.” These changes were made three months before singer FKA Twigs filed a lawsuit against LaBeouf over alleged sexual battery and abuse during their relationship.

Wilde had shortlisted Styles to play the character of Jack in LaBeouf’s stead after seeing his performance in Christopher Nolan’s Dunkirk. Wilde gave an interview for Styles’ November 2020 Vogue cover, speaking about her and the film’s costume designer Arianne Phillips’ excitement about having the singer on board.

“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,” Wilde said at the time.

“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.”

Since the incident on Tuesday neither Wilde nor Sudeikis have commented on the custody arrangement of their two children. Olivia is currently living in the UK with Styles while Sudeikis films the third series of the comedy drama Ted Lasso in West London. Don’t Worry Darling is out in cinemas on 23 September.

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