Inside Jason Sudeikis and Olivia Wilde’s Messy Custody Battle: A Complete Timeline

Credit: Matt Baron/Shutterstock

Inside Jason Sudeikis and Olivia Wilde's Messy Custody Battle: A Complete Timeline

Jason Sudeikis and Olivia Wilde kept their romance relatively private when they were together, but the details of their split became very public when they began a custody battle for their two children. The Saturday Night Live alum and the Booksmart director, who called it quits in November 2020, share son Otis (born in April 2014) and daughter Daisy (born in October 2016). The former couple have remained tight-lipped about the circumstances of their breakup, but in April 2022, the duo made headlines when Wilde was publicly served with legal papers during an appearance at CinemaCon. “Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” a source exclusively told Us Weekly at the time, noting that the Ted Lasso star didn't know when the documents would be delivered. “He would never condone her being served in such an inappropriate manner.” [sendtonews type="float" key="ePJ318YXKz-2832498-14453"] Before their split, the Drinking Buddies actress said that she felt having children represented a more powerful commitment than marriage. She and the Horrible Bosses star got engaged in 2013 after two years of dating, but they never walked down the aisle. “We are seriously connected,” Wilde told Net-a-Porter’s Porter Edit in February 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.’" Though their romance didn't last, the exes initially didn't have any problems with coparenting. “They’re doing their best at giving their kids a normal life," an insider told Us in July 2021. "The kids bring them back together since they are and always will be their number one priority.” The source added that the pair are "better off as friends," but they had been "coparenting well" after their breakup. That seemed to change in 2022, however, when Sudeikis served his ex with custody documents — and Wilde fired back in a court filing of her own. “Jason’s actions were clearly intended to threaten me and catch me off guard," the House alum alleged in her August 2022 response, per the Daily Mail. "He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible. 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." Keep scrolling for a complete timeline of Sudeikis and Wilde's custody battle.

Credit: Matt Baron/Shutterstock

Inside Jason Sudeikis and Olivia Wilde's Messy Custody Battle: A Complete Timeline

Jason Sudeikis and Olivia Wilde kept their romance relatively private when they were together, but the details of their split became very public when they began a custody battle for their two children. The Saturday Night Live alum and the Booksmart director, who called it quits in November 2020, share son Otis (born in April 2014) and daughter Daisy (born in October 2016). The former couple have remained tight-lipped about the circumstances of their breakup, but in April 2022, the duo made headlines when Wilde was publicly served with legal papers during an appearance at CinemaCon. “Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” a source exclusively told Us Weekly at the time, noting that the Ted Lasso star didn't know when the documents would be delivered. “He would never condone her being served in such an inappropriate manner.” [sendtonews type="float" key="ePJ318YXKz-2832498-14453"] Before their split, the Drinking Buddies actress said that she felt having children represented a more powerful commitment than marriage. She and the Horrible Bosses star got engaged in 2013 after two years of dating, but they never walked down the aisle. “We are seriously connected,” Wilde told Net-a-Porter’s Porter Edit in February 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.’" Though their romance didn't last, the exes initially didn't have any problems with coparenting. “They’re doing their best at giving their kids a normal life," an insider told Us in July 2021. "The kids bring them back together since they are and always will be their number one priority.” The source added that the pair are "better off as friends," but they had been "coparenting well" after their breakup. That seemed to change in 2022, however, when Sudeikis served his ex with custody documents — and Wilde fired back in a court filing of her own. “Jason’s actions were clearly intended to threaten me and catch me off guard," the House alum alleged in her August 2022 response, per the Daily Mail. "He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible. 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." Keep scrolling for a complete timeline of Sudeikis and Wilde's custody battle.

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November 2020

Us confirmed that the Virginia native and the Tron: Legacy star called it quits after nearly a decade together. “They’ve been separated for months now and there really is no drama. They’re handling this like adults,” a source told Us at the time. “It’s all about coparenting their kids, Daisy and Otis. That’s the priority for them.”

The insider also noted that the couple's bicoastal lifestyle had become a source of tension. "Jason loved living in New York and Olivia, who was born in NYC, was leaning more toward Los Angeles,” the source explained. “She was also busier than him at times, which was difficult at times. They butted heads on many occasions and decided it was best to go their separate ways.”

Despite the breakup, the insider told Us that the duo remained relatively amicable. "No one expects any big money grab or custody battle,” the source said. “Olivia has a very promising directing and producing career and Jason has films lined up.”

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January 2021

The O.C. alum was spotted holding hands with Harry Styles while attending the wedding of his manager, Jeffrey Azoff. An insider told Us at the time that the Grammy winner referred to Wilde as his "girlfriend" during a speech. Months earlier, the "Watermelon Sugar" singer had replaced Shia LaBeouf in Wilde's film Don't Worry Darling, which she directed.  

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December 2021

After her relationship with Styles made headlines all year, the Richard Jewell actress defended her new romance in a cover interview for Vogue. “Parenting forces you to be honest about how you live your life. It puts in sharp, clear focus decisions you’re making,” she explained. “I think we owe it to children to be happy. They sense it. They’re so intuitive. The idea that you can trick your kids into thinking you’re happy is ludicrous.”

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April 2022

During a Don't Worry Darling event at CinemaCon, Wilde was handed a manila envelope marked with the phrase "personal and confidential." While on stage in Las Vegas, the New York native asked, "Is this for me?" Us confirmed that the envelope contained documents relating to custody of Otis and Daisy. CinemaCon's managing director Mitch Neuhauser later told Us that the convention was rethinking its security protocols after the incident.

"We have never in the history of the convention had an incident where a delegate has approached the stage who was not authorized to be there,” he explained. “In light of this incident, we are reevaluating our security procedures to ensure the safety of all our attendees.”

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August 2022

Wilde slammed her ex-fiancé in court documents she filed about the pair's custody arrangement. According to the Daily Mail, the Cowboys & Aliens star and Sudeikis had previously agreed to let the kids finish the school year in Los Angeles while he filmed Ted Lasso in London. "Recently, however, Jason decided that he wanted to go to New York for the next year while he is not working, and wanted the children to be with him there during this time off," Wilde claimed in her filing. "When I did not agree, since the children have not lived in New York for several years, Jason filed these papers."

Though an insider previously told Us that Sudeikis had no knowledge of when or how the April 2022 custody papers would be served, Wilde alleged that the "outrageous legal tactics" were a calculated move. “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," she claimed. "Since Jason has made it clear that we will not be able to work this out for our children’s sake outside of the court system, I filed a petition for custody in Los Angeles.”

Sudeikis, for his part, reportedly argued that he didn't want the papers to be served at Styles' house in case Otis and Daisy were there when it happened. “I did not want service to take place at the children’s school because parents might be present," the We're the Millers star continued. "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."

The Emmy winner also wrote that he originally served the papers because of what Wilde said she would do if Sudeikis tried to move the kids to NYC. “First, Olivia said that if I did not reside full-time in Los Angeles, she would allow me to spend time with Otis and Daisy on weekends and during vacation periods — thus depriving me of my right to parent the children during important periods of their lives,” the 30 Rock alum claimed. “Second, Olivia said that she intended to relocate with the children to London following the close of school in 2023.”

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August 2022

Wilde broke her silence on her battle for custody during a candid Variety profile, arguing that the public service of the documents was an attempt to "sabotage" her CinemaCon presentation. "In any other workplace, it would be seen as an attack. It was really upsetting," she told the outlet. "It shouldn’t have been able to happen."

She went on to call the incident "appalling," describing how Otis and Daisy will be impacted by the drama. "The only peo­ple who suffered were my kids, because they'll have to see that, and they shouldn't ever have to know that happened," she added. "For me, it was appalling, but the victims were an 8 and 5 year old, and that's really sad. I chose to become an actress; I willingly walked into the spotlight. But it's not something my children have asked for. And when my kids are dragged into it, it's deeply painful."

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March 2023

Wilde slammed Sudeikis ahead of another hearing about the duo's custody battle, claiming that he blindsided her with a New York appeal of last year's decision that the children should remain in California. "Apparently he had learned that the court date for our first appearance was January 4, 2023, and purposefully did not advise me of it, nor did his lawyer advise my lawyers. Not knowing the date, neither I nor my lawyers appeared," she claimed in court docs obtained by the Daily Mail. "Jason's] underhandedness and bad faith in these proceedings is astounding. I am completely perplexed at why he believes that engaging in intimidation or trickery will serve him or our children's best interests."

The Babylon actress also accused her ex of acting in "bad faith" when it comes to the future of their children. "Jason should not be permitted to litigate Olivia into debt, and then claim she should be deprived of her right to seek a needs-based fee contribution from him," her legal team wrote. "While the details of Jason's finances are presently unknown as he refused to substantively respond to basic discovery, she is aware that he is far wealthier than she is."