Olivia Wilde and Jason Sudeikis’ Relationship Timeline

Rollercoaster relationship. Olivia Wilde and Jason Sudeikis went from one of Hollywood’s most solid couples to exes in the middle of a messy custody battle.

The Don’t Worry Darling director and Ted Lasso star first met while attending a Saturday Night Live finale party in May 2011.

They became engaged in January 2013, while they welcomed their first child, son Otis, in 2014 and second child, daughter Daisy, in 2016.

Despite being engaged, Jason insisted that they weren’t in a rush to tie the knot. “We are seriously connected,” she told The EDIT in 2016. “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.’”

In November 2020, Olivia and Jason shocked the world when they announced they had split and called off their seven-year engagement. “The split happened at the beginning of the year,” a source close to the duo revealed to People at the time. “It’s been amicable, and they’ve transitioned into a great coparenting routine. The children are the priority and the heart of the family’s relationship.”

Jason later reflected on their split during an interview with GQ magazine in June 2021.

After admitting he hit “rock bottom” following their split, Jason said he was still processing everything that went down. “I’ll have a better understanding of why in a year, and an even better one in two, and an even greater one in five,” he told the publication. “It’ll go from being … a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle.”

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“That’s an experience that you either learn from or make excuses about,” the We’re the Millers actor continued. “You take some responsibility for it, hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it.”

Now that the couple has called it quits, they have found themselves in the middle of a nasty custody battle.

Keep scrolling to see Olivia and Jason’s relationship timeline.

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October 2012

The couple took the next step in their relationship by moving in together. While speaking to USA Today, Olivia revealed that she relocated to from Los Angeles to New York City to live with Jason.

“I’ve been decorating our new apartment. That’s a lot of what I do, too. I’m so domestic,” she said at the time. “We have a cool new electronic drum kit. It’s a good life. For years, I worked constantly. I was doing the show and doing movies on the weekends,” she added, referring to her role on the Fox show House.

May 2022

In Touch exclusively reported that Jason had an issue with Olivia and Harry’s relationship.

“Olivia is pretty much convinced that Jason has an issue with her dating Harry and is being deliberately tricky because of it, that he still bears a grudge because she moved on with Harry so quickly after they split and is happy,” a source explained.

The insider added that Olivia was “furious” that Jason had her served with custody documents at CinemaCon. “Olivia didn’t know what the hell was going on when it happened and was furious,” they continued. “The way Olivia sees it, even if she’d been served off stage, it would’ve still been embarrassing because she was surrounded by fans and all her people.”

August 2022

Olivia filed her own documents regarding custody, noting that she and Jason disagreed on where to raise their children.

“The fact that Jason would embarrass me professionally and put our personal conflict on public display in this manner is extremely contrary to our children’s best interests,” the Year One actress alleged in a court filing obtained by the Daily Mail, adding that he “clearly intended to threaten me and catch me off guard.”

“He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible,” Olivia added.

Jason responded by addressing the drama of Olivia being served at CinemaCon. “I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present,” he reportedly wrote, referring to the “As It Was” singer.

“I understand that the process server had only done her job; however, I deeply regret what happened. Olivia’s talk was an important event for Olivia, both professionally and personally, and I am very, very sorry that the incident marred her special moment,” he added.

August 2022

The O.C. actress won her request to keep the custody battle in California, with the judge determining it is the primary residence of the former couple’s children. Jason had asked for the case to be heard in New York, as he lives in Brooklyn and wants Otis and Daisy to reside with him there.

“Judge Powell and this Referee agreed that New York was not the home state of the subject children; but rather California was the children’s home state,” read a legal filing signed by Danielle M. Rodriguez, Esq. Court Attorney-Referee on August 5, obtained by Page Six on August 10.

The legal paperwork added, “This court finds that New York does not have jurisdiction to hear the custody petitions as New York is not the home state of the subject children.”