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The $27,500 Question: 5 Shocking Truths About Olivia Wilde And Jason Sudeikis' Amicable Co-Parenting Era

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The tumultuous chapter of Olivia Wilde and Jason Sudeikis' high-profile split and subsequent custody battle appears to have finally closed, paving the way for a surprisingly amicable co-parenting relationship that has Hollywood buzzing. As of this current date, December 20, 2025, the former couple has transitioned from courtroom drama and public feuds to a functional and friendly dynamic, often spotted sharing warm exchanges in Los Angeles.

This dramatic shift is a testament to their shared commitment to their two children, Otis and Daisy, despite the intense scrutiny and legal battles that dominated headlines for years. The latest updates reveal a settled financial arrangement and a joint custody schedule that prioritizes stability, proving that even the most bitter celebrity breakups can evolve into a mature, working partnership.

Olivia Wilde & Jason Sudeikis: Essential Biographical Profiles

To fully understand the current dynamic, it is important to look back at the key biographical and career milestones of the two stars who first met on the set of Saturday Night Live in 2011.

Olivia Wilde (Born Olivia Jane Cockburn)

  • Role: Actress, Director, Producer, Activist.
  • Born: March 10, 1984, in New York City, New York.
  • Key Projects: House (as Dr. Remy "Thirteen" Hadley), Tron: Legacy, Booksmart (Directorial Debut), Don't Worry Darling (Director/Actress).
  • Parents: Leslie Cockburn (Journalist/Producer) and Andrew Cockburn (Journalist).
  • Early Life: Attended Phillips Academy in Andover, Massachusetts.
  • Relationship Timeline: Married Tao Ruspoli (2003–2011); Engaged to Jason Sudeikis (2013–2020); Dated Harry Styles (2021–2022).
  • Current Status: Reportedly dating former professional basketball player and actor Dane DiLiegro.

Jason Sudeikis (Born Daniel Jason Sudeikis)

  • Role: Actor, Comedian, Writer, Producer.
  • Born: September 18, 1975, in Fairfax, Virginia.
  • Key Projects: Saturday Night Live (Cast Member/Writer), Horrible Bosses, We're the Millers, Ted Lasso (Creator/Star/Executive Producer).
  • Parents: Kathryn Sudeikis (Travel Agent) and Daniel Joseph Sudeikis (Vice President of Business Development).
  • Early Life: Grew up in Overland Park, Kansas.
  • Relationship Timeline: Married Kay Cannon (2004–2010); Engaged to Olivia Wilde (2013–2020).
  • Current Status: Reportedly dating model Elsie Hewitt.

The Custody Settlement: $27,500 and a Week-on, Week-off Schedule

The biggest news surrounding the former couple in the past two years was the finalization of their intense child custody dispute. The legal battle, which began with Sudeikis famously serving Wilde with documents onstage at CinemaCon in April 2022, was a protracted and public affair that Wilde later called "traumatic."

The resolution, reached in September 2023, established a clear, structured co-parenting plan that has since brought stability.

The Financial Arrangement

In a move that drew significant media attention, the court ordered Ted Lasso star Jason Sudeikis to pay a substantial sum in child support.

  • Child Support Amount: $27,500 per month.
  • Purpose: This payment is intended to cover the children's expenses, including private school tuition and extracurricular activities.
  • Context: The high figure reflects the significant income disparity between the two stars, particularly Sudeikis' lucrative earnings from the critically acclaimed Apple TV+ series Ted Lasso.

The Joint Custody Agreement

Beyond the financial details, the settlement established a precise schedule for their joint custody of son Otis (born 2014) and daughter Daisy (born 2016).

  • Custody Type: Joint physical and legal custody.
  • Schedule: The parents operate on a "week-on, week-off" rotating schedule. This arrangement is common for co-parents living in close proximity, which they both do in Los Angeles.

This structured agreement has been key to reducing conflict, allowing both Wilde, a successful director of films like Don't Worry Darling, and Sudeikis, an Emmy-winning actor, to manage their demanding Hollywood careers while maintaining a strong presence in their children's lives. The transition to a "good space," as sources have described it, is a direct result of this legal finality.

From Public Feud to Friendly Hugs: The Current Dynamic in L.A.

Perhaps the most surprising and recent development is the palpable improvement in the former couple's personal relationship. After years of tension, the two have demonstrated a commitment to civility for the sake of their family.

A widely circulated photo from April 6, 2025, showed the ex-fiancés sharing a friendly hug in Los Angeles. This moment of genuine warmth, nearly two years after the custody settlement, signaled a definitive end to the public hostility and a successful pivot to amicable co-parenting.

Sources close to the couple have confirmed that they are successfully co-parenting, which is facilitated by both of them residing in L.A. The ease with which they can hand off their children, Otis and Daisy, minimizes stress and maximizes the consistency of their children's routine. This focus on the children's well-being is the ultimate goal of any joint custody arrangement and a positive example for other high-conflict Hollywood breakups.

Navigating New Romances and the Co-Parenting Landscape

Both Olivia Wilde and Jason Sudeikis have moved on to new romantic relationships, which adds another layer to their co-parenting arrangement. The maturity of their current dynamic is demonstrated by their ability to maintain a respectful relationship even as they date other people.

Olivia Wilde's New Chapter

Following her highly publicized relationship with pop star Harry Styles, Wilde has reportedly begun dating Dane DiLiegro. DiLiegro, a former professional basketball player who also acts (known for his roles in creature suits), represents a new phase in Wilde's personal life. The shift from the intense spotlight of the Styles relationship to a more private romance suggests a desire for greater stability, which is beneficial for her children.

Jason Sudeikis' Transformation

Jason Sudeikis, who channeled some of his post-split pain into the emotional depth of Ted Lasso, is reportedly dating model Elsie Hewitt. Sources suggest that Sudeikis has undergone a "huge transformation" since the split, becoming "a lot more confident." This personal growth and newfound confidence are crucial for maintaining a healthy co-parenting environment, demonstrating emotional resilience to his children.

The ability of both Sudeikis and Wilde to successfully integrate new partners into their lives while maintaining a unified front for Otis and Daisy is a key indicator of their long-term co-parenting success. The focus remains on the children, ensuring that the new partners understand and respect the established week-on, week-off schedule and the joint custody agreement.

The Legacy of a Hollywood Power Couple

The relationship between Olivia Wilde and Jason Sudeikis, which began in 2011 and saw them engaged for seven years before splitting in 2020, will forever be a part of Hollywood lore.

Their story is a powerful case study in how celebrity couples handle separation under the unforgiving glare of the media. While the initial fallout was messy—marked by the CinemaCon incident and legal leaks—the current status is a testament to the power of settling differences for the greater good of the family.

The $27,500 child support figure and the joint custody details are now public record, but the most important update is the sight of the two sharing a friendly hug. It signifies that the era of conflict is over, and the new era of amicable co-parenting for Otis and Daisy Sudeikis is firmly underway in Los Angeles. This mature approach to their post-engagement life ensures that both stars can focus on their thriving careers—Wilde in directing and Sudeikis in his continued success with projects like Ted Lasso—without the constant distraction of a bitter legal battle.

olivia wilde & jason sudeikis
olivia wilde & jason sudeikis

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