Olivia Wilde Reveals What Went Wrong With Jason Sudeikis After ‘Really Vicious’ Custody Drama

Olivia Wilde and Jason Sudeikis once looked like one of Hollywood’s strongest couples, but their nearly decade-long relationship ended in a painful breakup that later turned into a very public custody battle.

Years after their split, Wilde has reflected on what went wrong between them, including the moment she says crossed the line when she was publicly served custody papers during CinemaCon.

Olivia Wilde and Jason Sudeikis’ Fairytale Romance Slowly Fell Apart

Wilde and Jason Sudeikis first met at a Saturday Night Live finale party in May 2011, and the connection was immediate. Wilde later admitted she found the comedian “charming” the first time they met. “He’s a great dancer and I’m a sucker for great dancers. But he didn’t even get my number“.

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Although Sudeikis did not ask for her number that night, the pair kept crossing paths over the next six months. Sudeikis later told Stephen Colbert in 2017 that they “hit it off that night.” After one of Wilde’s friends passed along her phone number, he finally texted her and asked her on a date.

Their relationship moved quickly, and by October 2012, Wilde revealed they were living together in New York with their rescue dog. She even told USA Today, “I’ve been decorating our new apartment. That’s a lot of what I do. I’m so domestic.” Less than two years after they began dating, Sudeikis proposed in January 2013.

As their engagement continued, Wilde often spoke about wanting a family. In an interview, she explained, “There’s no strict plan for anything in my life. What happens, happens.” Although she was not rushing into motherhood, she hoped to have three children someday.

Instead, the couple welcomed two children during their relationship. Their son, Otis Alexander, was born on April 20, 2014, and their daughter, Daisy Josephine, arrived on October 11, 2016. Before Daisy’s birth, Wilde shared her excitement about having more children, telling People, “I love my siblings so much, and Jason has incredible siblings too. The more the merrier.”

Custody Battle Exposed Their Deepest Problems

Despite building a family together, the relationship eventually came to an end. In November 2020, reports confirmed that Wilde and Sudeikis had called off their engagement after nearly 10 years together. They both moved on afterward, with Wilde dating Harry Styles and Sudeikis beginning a relationship with Keeley Hazell.

In case you missed it: “It Was Crazy”: Olivia Wilde Reflects On The Public Fallout Of Her Relationship With Much Younger Harry Styles

The split became far more bitter in April 2022 when Wilde was unexpectedly served custody papers while presenting onstage at CinemaCon. The envelope was marked “Personal and Confidential,” and according to a source, the actress was left “surprised and embarrassed” by the public moment.

Even so, Wilde finished her presentation before later challenging Sudeikis’ custody petition. She argued that the “aggressive” way the documents were served embarrassed her “professionally.” Months later, Wilde spoke openly about the incident. She described the move as an attempt to “try to sabotage” her and called it “really vicious.”

She added, “But I had a job to do; I’m not easily distracted. But, you know, sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship.” The former couple eventually settled their custody dispute in September 2023, agreeing to share their children on a “week-on, week-off basis.”

More recently, Wilde revisited the painful chapter during the June 16 episode of the Call Her Daddy podcast. Describing the custody battle, she recalled, “Take the kids away from her forever and burn her to the ground.” She also criticized the public response, saying, “The double standard … It was nuts.”

Although Olivia Wilde and Jason Sudeikis have now settled their custody case and share joint custody of their two children, the actress has made it clear that the public legal battle remains one of the most painful chapters of her life.

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