Jason Sudeikis & Olivia Wilde Drama Timeline: He’s ‘Not Paying’ Child Support

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The Don’t Worry Darling director and the Ted Lasso creator were together for 9 years and are currently embroiled in a long custody battle hearing for their two children, Otis, born in 2014 and Daisy, born in 2015. Here’s a timeline of the Olivia Wilde and Jason Sudeikis drama that’s currently happening to catch you up.

During the episode interview on The Kelly Clarkson Show that aired on September 21, 2022, Wilde was asked about how being a single mom affects her kids and she talked about the challenges it had on her family. “It’s allowed for some really deep conversations with my kids about emotions and about happiness and about what family means and love,” Wilde explained about her two kids with Sudeikis (who she refers to only as her ex), Otis, 8 and Daisy, 5. “It’s actually allowed me to get to know them in a different way. My priority is them, as long as they’re happy and they’re healthy. My ex and I agree on that. They’re our everything to us. She then elaborated on how there are different families where their situation is “hard but doable” for them “There are so many families that are blended and different shapes. If you can surround them with so much love, then it’s OK. But it’s tricky because we’re not doing it in private.”

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So what’s going on with the Olivia Wilde and Jason Sudeikis drama that’s happening? Read more below to find out.

Olivia Wilde & Jason Sudeikis Custody Battle Timeline

April 2023: Olivia accuses Jason doesn’t pay her child support

Image: Theo Wargo/Getty Images for IFP
Image: Theo Wargo/Getty Images for IFP

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In court documents obtained by The Blast, Olivia wrote, “Jason is not currently paying child support to me, despite my requests through counsel that we agree upon an interim support amount to avoid further litigation in this matter,” the Drinking Buddies actress alleged. “While Jason and I have been splitting certain expenses for the children, such as their school tuition, I have been bearing 100 percent of the costs of the children’s care when they are with me, including, but not limited to, their food, clothing, childcare, extracurricular activities and transportation costs.”

She claimed that the Ted Lasso creator has a “significantly superior position” to her when it comes to finances. “While I have yet to receive specific financial information from Jason, my understanding and belief is that he is wealthier than I am and has far greater income,” Wilde wrote, requesting $500,000 toward legal costs. “I have no reason to believe that Jason would dispute this.”

Olivia’s legal team, meanwhile, alleged that she “has borne the lion’s share of the expenses for their children” and asked that Sudeikis pay child support “retroactive” to the date she filed the case.

The outlet reports that Olivia told the court she made over $40,000 a month in salary, including another $60,000 from Wilde Company income and rental property income. Also, she has $645,187 in bank accounts and over $107,000 in other assets. Olivia has said she has over $107,000 in monthly expenses.  

March 2023: Olivia has a major victory in the custody hearing

Image: Dia Dipasupil/Getty Images
Image: Dia Dipasupil/Getty Images

In March of 2023, a judge ruled in favor of Olivia to have the custody hearing in Los Angeles, California versus Jason’s preference for New York City where he wants the kids to go to school to.  “The Court finds that it is in the interest of substantial justice that the parties’ child support petition be heard in California,” a statement obtained by TMZ said.

March 2023: Olivia and Jason Embrace At Otis’ soccer game

Image: Matt Winkelmeyer/Getty Images for Critics Choice Association)
Image: Matt Winkelmeyer/Getty Images for Critics Choice Association)

According to sources who told Daily Mail on March 18, 2023, the former couple has put their differences aside from them as insiders say that now they are in “constant communication” and the outlet even photographed the couple embracing each other at their son’s soccer game.

March 2023: Jason & Olivia’s custody hearing begins

Image: Gregg DeGuire/WireImage
Image: Gregg DeGuire/WireImage

Olivia and Jason’s court hearing was expected to be in the third week of March 2023, but was postponed. In court documents obtained by the Daily Mail, Olivia’s lawyers wrote, “While Jason can afford to spin his wheels with filing after filing, Olivia cannot,’ her lawyers wrote in advance of a hearing scheduled in Los Angeles for today, which has now been canceled.”

Her lawyers continued, “Jason seems intent on throwing whatever he can against the wall to see what will stick, and this Request for Order seeking a stay of the California Parentage action is just the latest example. 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 attorneys write.

October 2022: The Nanny Salad Dressing Saga

Image: Frazer Harrison/Getty Images
Image: Frazer Harrison/Getty Images

According to an interview with Daily Mail, an anonymous nanny of Olivia and Jason’s children recalled the night that things ended between Jason and Olivia. “On the Monday morning [of] Nov. 9, when I came back from a weekend off, [Jason] was crying a lot, crying and crying. I didn’t know what had happened at all,” the nanny claimed. “After I’d got the kids ready, Jason came upstairs and was having some coffee. He was crying and a mess, saying, ‘She left us. She left us!’” The nanny also alleged that Jason banned the staff from listening to Harry’s music.

Things reached a breaking point when Olivia left the house with a salad with her “special dressing” to give to the “As It Was” singer. “The night she left with her salad, Jason had chased after her, videotaping her in the house,” she recalled. “She was saying: ‘I’m scared of you, Jason, I’m scared of you.’ And he said: ‘If you’re scared of me, why are you leaving your kids with me? So then, Jason went outside and lay under her car so she wouldn’t leave. She got in her car to back up, he lay under her car so she wouldn’t leave.” The nanny continued, “He said he was doing it on purpose to make her late going to see Harry.” It was the last straw for the SNL alum. “Out of everything, he was like, ‘She made her special salad dressing and took it to him.’”

When the story went viral, Olivia responded with a cryptic salad dressing on her Instagram story from the book Heartburn by Nora Ephron. She and Jason later responded to the Nanny allegations in a joint statement to E! News. “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly.” They accused the nanny of launching a “18 month long campaign of harassing us, as well as loved ones, close friends and colleagues,” the duo added that the allegations have “reached its unfortunate apex.”

August 2022: Olivia denies she cheated on Jason with Harry

Image: Neil Mockford/GC Images
Image: Neil Mockford/GC Images

Olivia put the cheating rumors to rest when she described it as “complete horse shit” in a September Vanity Fair cover profile. “Our relationship was over long before I met Harry. Like any relationship that ends, it didn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic,” she said at the time. “We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to NOT, because we could be better parents as friends who lived in different houses.”

She also told the entertainment outlet about how she felt about the CinemaCon incident. “To try to sabotage that was really vicious. But I had a job to do; I’m not easily distracted,” she told Variety in late August 2022. “But, you know, sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship.” Wilde expanded on the custody papers moment in more detail with Vanity Fair, saying it was behavior “consistent” in her knowledge of Sudeikis’ past behavior, as well as it being damaging to her children to see their mother so publicly humiliated. “Unfortunately, that was consistent with my experience of the relationship. So I was probably the least shocked. But I was also deeply saddened by it—and disturbed by it in lots of ways.” She continued, explaining that her being issued custody papers in such a way had to be premeditated for the amount of effort involved. “I know it took an extraordinary amount of energy [for the server] to get in that room. It took a tremendous amount of forethought,” she said. “And I will tell you, there are so many other ways to do that. I am not someone who lives in hiding. If that experience hadn’t been public, I never would have spoken of it, because I never would want my kids to know that happened. Unfortunately, they will know that happened.”

April 2022: A source close to Jason denies he had knowledge of the CinemaCon incident

Image: Frazer Harrison/Getty Images
Image: Frazer Harrison/Getty Images

A source told The Hollywood Reporter on April 27, 2022, that Jason wasn’t aware that his ex-fiancée would be served custody papers in public while at CinemaCon. “Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” the insider said. “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.”

Later in court documents, Jason explained why he didn’t want to serve his ex-girlfriend in front of their kids,  “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.”

April 2022: Olivia Is Given Custody Papers On Stage at CinemaCon

Image: Getty Images
Image: Getty Images

Olivia Wilde was on stage in front of 3,000 audience members at CinemaCon in Las Vegas on April 27, 2022, when a woman interrupted her as she read from a teleprompter to give her a manila envelope, which was labeled with the words “Personal and Confidential.” “This is for me?” Wilde said in the middle of her presentation for Don’t Worry Darling at The Colosseum at Caesars Palace. “Is this for me?”

The House alum proceeded to comment about how the envelope was “very mysterious” before telling the crowd that she was “going to open it now because it feels like it’s a script.” When she opened the envelope and saw they were custody papers from Sudeikis, whom she split from in 2020 after nine years together, Wilde put the papers back in the envelope and said, “OK, got it. Thank you.” She continued her presentation on Don’t Worry Darling and didn’t talk about the envelope again.

December 2021: Olivia goes public with Harry Styles

Image: Dominique Charriau/WireImage
Image: Dominique Charriau/WireImage

In a Vogue cover story, she briefly talked about her then-speculative relationship with Harry Styles. “It’s obviously really tempting to correct a false narrative,” she told the outlet of the attention surrounding their romance. “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.” She concluded, “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.”

September 2021: Olivia gushes about being a single mom

Getty Images.
Getty Images.

“It’s allowed for some really deep conversations with my kids about emotions and about happiness and about what family means and love,” Olivia explained about her two kids with Jason (who she refers to only as her ex),. “It’s actually allowed me to get to know them in a different way. My priority is them, as long as they’re happy and they’re healthy. My ex and I agree on that. They’re our everything to us. She then elaborated on how there are different families where their situation is “hard but doable” for them “There are so many families that are blended and different shapes. If you can surround them with so much love, then it’s OK. But it’s tricky because we’re not doing it in private.”

November 2020: Olivia and Jason Split

Image: McBride/Getty Images
Image: McBride/Getty Images

In November 2020, Olivia and Jason reportedly split. They became engaged in 2013. “They’ve been separated for months now and there really is no drama. They’re handling this like adults,” a source told Us Weekly 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 fought over their bicoastal lifestyle. “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.”

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