What Went Wrong in Olivia Wilde and Jason Sudeikis' Relationship? Inside Their Nearly 10-Year Romance and Split

Olivia Wilde and Jason Sudeikis were together for nearly a decade.

The ex-couple's connection was immediate when they first crossed paths at a finale party for Saturday Night Live in May 2011.

According to Wilde, she thought Sudeikis was "charming" when she met him.

"He's a great dancer and I'm a sucker for great dancers. But he didn't even get my number," she told Allure.

Although Sudeikis did not get her number at the time, the duo kept bumping into one another over the next six months.

Meanwhile, the comedian told Stephen Colbert in 2017 he and Wilde "hit it off that night."

After Wilde's guy friend gave her number to Sudeikis, he texted her and finally asked her on their first date that same year.

Following their PDA-packed outings, Wilde confirmed she was living with Sudeikis and their rescue dog in New York City.

"I've been decorating our new apartment. That's a lot of what I do," she told USA Today in October 2012. "I'm so domestic."

The Hall Pass, Horrible Bosses actor then proposed to the filmmaker in January 2013 after less than two years of dating.

In April 2013, Wilde revealed she wanted to have three children with her then-fiancé. However, she also noted she was not in a rush to have kids at the time.

"There's no strict plan for anything in my life. What happens, happens," she told Marie Claire.

During their nearly 10-year relationship, Wilde and Sudeikis welcomed two children: son Otis Alexander, born on April 20, 2014, and daughter Daisy Josephine, born on October 11, 2016.

Before their second child was born, the Conversations With Other Women actress teased she was "desperate for more kids."

"I love my siblings so much and Jason has incredible siblings too. The more the merrier," she told People.

In November 2020, a news outlet reported Wilde and Sudeikis had split and called off their engagement.

Both moved on after the breakup: Wilde with Harry Styles, and Sudeikis with Keeley Hazell.

"That's an experience that you either learn from or make excuses about," the Ted Lasso star said in a July 2021 interview with GQ. "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."

Wilde and Sudeikis' split took a turbulent turn when the Don't Worry Darling director was served with legal documents from her ex-fiancé while onstage at CinemaCon in April 2022.

According to a source, Wilde was "surprised and embarrassed" after receiving the envelope that had the mark "Personal and Confidential" in public.

"Olivia was professional and adult about what happened and made sure the show went on," the insider told People.

She then filed to dismiss Sudeikis' petition for custody of their children, saying he embarrassed her "professionally" due to the "aggressive" manner of serving the papers.

In August 2022, Wilde directly addressed the ordeal during an interview with Variety. At the time, she pointed out that to "try to sabotage" was "really vicious."

"But I had a job to do; I'm not easily distracted," she continued. "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 and Sudeikis finally settled their custody case in September 2023. They agreed to have joint custody of their children on what was described as a "week-on, week-off basis."

Over five years after the split, Wilde spoke candidly about her tumultuous romance with Sudeikis on the June 16 episode of the "Call Her Daddy" podcast.

"Take the kids away from her forever and burn her to the ground," she added. "The double standard … It was nuts."

During the same podcast appearance, Wilde also looked back at the "loveliest relationship" she had with Styles.

"It really did upset people," she said of the backlash after she began dating the young singer. "People were f------ p-----!"