Olivia Wilde and Jason Sudeikis’ Relationship Timeline: What Led Up to Their Custody Battle

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Olivia Wilde and Jason Sudeikis have gone from friendly exes co-parenting their two children to waging a legal war in a bitter custody battle that's now dragging out in public. And, based on recent legal filings from both legal teams, there seems to be no end in sight.

The Don't Worry Darling director and Ted Lasso star currently find themselves in court fighting over where their two children -- Otis, 8, and Daisy, 5 -- will live. Wilde would like to be based in Los Angeles and potentially London, where her boyfriend, Harry Styles, resides. Sudeikis wants to live with his kids in Brooklyn.

As if that wasn't already a challenging hurdle, there's also the manner in which Sudeikis' lawyers chose to serve Wilde custody papers, actions she deemed "were clearly intended to threaten me and catch me off guard." Wilde also described being served custody papers while on stage at CinemaCon back in April as "the most aggressive manner possible."

It didn't used to always be this way. The former couple had a classic meet-cute story, by Hollywood standards, and in the years that followed, the couple would become engaged and parents to two lovely children.

With their custody battle playing out in court, ET takes a closer look at how we got here.

Wilde and Sudeikis meet in 2011

They first met while at a Saturday Night Live finale party in May 2011. According to Sudeikis, they "hit it off that night" but it would take a while -- coupled with a friend getting in the middle of things -- before they'd exchange numbers.

Wilde told Allure in October 2013 that when she first met Sudeikis she "thought he was so charming."

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

According to the magazine, they kept running into each other until, finally, one of her guy friends straight-up walked up to the actor and said to him, "This is Olivia's number. Use it." Wilde added, "That was the beginning."

Wilde later revealed on The Howard Stern Show in 2016 that Sudeikis didn't text her until a month after getting her phone number. She joked, "I was like, 'You guys, did Jason Sudeikis die? Because I don't have any texts."

She also revealed that Sudeikis didn't kiss her until the fourth date. And, when he did, Wilde said she was head-over-heels.

Wilde relocates to NYC to live with Sudeikis 

In an October 2012 interview with USA TODAY, Wilde reveals it's at this time in her life that she had time to have a life, and also that she relocated from L.A. to Manhattan to live in a downtown apartment with Sudeikis. They also live with their rescue mutt, Paco.

"I've been decorating our new apartment. That's a lot of what I do, too. I'm so domestic. 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," said Wilde referring to the Fox hit show, House.

Sudeikis pops the question 

The Horrible Bosses star proposed to Wilde after the holidays in late 2012. She was 28 at the time and he was 38.

"They are so excited," said a source at the time. "And very, very happy."

Sudeikis 'roped in' to join Wilde in Drinking Buddies

In a 2013 interview with ABC News, Wilde reveals that Sudeikis' appearance in the comedy film wasn't planned.

"We roped him in," she said. "He didn't know he was gonna have to work. He came to visit me in Chicago before he went to shoot We're the Millers, and he came to lunch onset and I was like, 'Listen, we don't have anyone to play my boss, will you just jump in and improvise with me for an hour? And he's like, 'Yeah, great, let's go."

They welcomed their first child, a boy ...

Wilde and Sudeikis welcomed Otis Alexander Sudeikis on Wednesday, April 23, 2014.

The Rush actress made the announcement herself! The new mom tweeted: "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building.)"

... and then a girl!

In October 2016, Sudeikis and Wilde welcomed their second child, a girl. They named her Daisy Josephine Sudeikis.

"There goes the neighborhood. Daisy Josephine Sudeikis," Wilde announced alongside the adorable first photo of her baby girl. "Born, like a boss, on #internationaldayofthegirl."

They team up for Booksmart in 2019

Wilde directed Sudeikis for the coming-of-age comedy. It also marked her feature directorial debut. Speaking with ET in May 2019, Wilde joked that her relationship with Sudeikis was his audition for the film.

"His entire relationship with me has been one long audition for Booksmart and he nailed it," Wilde jokingly told ET's Deidre Behar at the time.

As far as directing Sudeikis, Wilde admitted she wasn't able to "completely" brush off the personal and put on the professional hat with him, but it was "remarkable" watching him behind the monitor.

"There's still a shorthand that comes from being someone's closest partner, but I loved being able to just set him free because he's one of the best improvisers in the world," she expressed. "And I just loved that we got him to take this bit of information that we had in the script and run with it."

"And he gave us so much," Wilde continued. "We were dying laughing behind the monitor the whole time. I was like, 'This is remarkable.' Not many people can do that, and I loved in the scenes with him, our girls, our two leads, Beanie and Kaitlyn, they're just looking at him like, 'How is he doing that?'"

Sudeikis and Wilde call off engagement

ET confirmed in November 2020 that they ended their engagement after seven years.

"There was absolutely no drama or scandal, they just didn’t work as a couple anymore," said a source at the time. "If you’re looking for a juicy story, there just isn’t one."

"Of course, their kids are their number one priority and at the forefront of any decision they make,” the source added, explaining that they are both 100% involved in their kids’ lives. 

“They adore each other and have nothing but the utmost respect for one another. They will continue to be each other’s biggest supporters, especially when it comes to parenting their children and their careers," the source shares. "They see each other all the time still."

The source noted that Wilde has remained very close with Sudeikis' sister, and added that the former couple moved out of their Brooklyn, New York, home at the end of 2019.

This was "the beginning of the end," the source said, adding that they had since relocated to Los Angeles.

Wilde and Styles spark dating rumors

The actress and singer were spotted holding hands as they attended a wedding together in the ritzy neighborhood of Montecito, California.

ET learned that they attended the wedding of Styles' manager, Jeffrey Azoff, who works in Artist Relations at Apple Music. 

Styles was also snapped in his bathrobe at one point, happily posing with Azoff and his bride, Glenne Christiaansen. A source told ET that Styles officiated the wedding.

According to TMZ, there were only 16 people present at the shindig, and Styles took Wilde as his plus one and they held hands throughout the event.

Wilde and Sudeikis reunite in L.A. 

Just hours after photos and video surfaced of Wilde and Styles looking very much like an item at a wedding, the actress and her ex-boyfriend reconnected when she was spotted visiting Sudeikis at his L.A. home.

Both Wilde and Sudeikis wore face masks when they met up, while the actress rocked a purple sweater with a white wide-brimmed hat, and the former Saturday Night Live star rocked a grey sweatshirt.

Wilde dating Styles was 'all very organic' 

A source told ET that the actress and singer grew close while working together on the set of their upcoming film, Don't Worry Darling, the psychological thriller she directed, which centers on an unhappy housewife in the 1950s and her husband's dark secret. 

"Olivia and Harry are together for long days on set and have gotten to know each other really well, so it's all very organic," the source said at the time.

According to the source, Wilde "wouldn't let a romantic relationship get in the way of a professional one, so anything they're doing is being done thoughtfully." While the romance may have come as a surprise to some, a source told ET that Sudeikis and Wilde "split almost a year ago."

"So it's not like she's rushing into something," the source added. "Olivia and Jason talk all the time and are still close because of the kids. It's highly unlikely he was blind-sided by this news."

"She's always liked Harry and it was one of the reasons she cast him and, since then, she's developed a thing for him," the source adds.

Sudeikis 'really hurt' by Wilde's romance with Styles

A source told ET in January 2021 that while the pair wanted to remain close after their split, the Ted Lasso star is "really hurt" by Wilde's new romance with Styles.

"Olivia and Jason ended amicably and both wanted to remain close and stay friends for the sake of their kids and because they have mutual respect and love for one another," ET's source said, explaining that Sudeikis had hoped he and Wilde "would eventually reconcile and get back together."

"He has been really hurt and somewhat jealous that Olivia has moved on with Harry," the source added.

Sudeikis and Wilde 'rebuilding their friendship' 

A source told ET in February 2021 that while Wilde is "so happy" in her new relationship with Styles, the actress is glad Sudeikis is now "in a good place, too." 

"Jason was initially really hurt about Harry and Olivia's relationship, but now that he's doing his own thing, things between him and Olivia have gotten better," the source said at the time. "They're rebuilding their friendship again and co-parenting together."

A second source told ET that Sudeikis and British model Keeley Hazel are currently "seeing each other, having fun and seeing where things go." The two have known each other for years, ever since meeting on the set of Horrible Bosses 2 in 2014.

Wilde and Styles inseparable

A source told ET in February 2021 that the pair, at the time, was in the United Kingdom following the wrap of Don't Worry Darling.

"Harry and Olivia have been inseparable," the source said. "Of course, that’s in part because they’ve been in a bubble for their film, but even in the days since it wrapped, they’re still spending all their time together."

The source noted that Sudeikis had their two kids in the U.K. while filming his show, Ted Lasso.

With Don't Worry Darling wrapped in Los Angeles, Wilde made her way across the pond to be with her children. Styles, who is from the U.K., decided to tag along, the source said. Styles and Wilde planned to quarantine and get tested for COVID-19 before being reunited with the kids, the source added.

Sudeikis opens up about the split

In the new cover story for GQ magazine, Sudeikis opened up about the wild year that saw him split with Wilde, who then went on to date Styles. At the time, he was also seeing Hazell.

“I’ll have a better understanding of why in a year,” he told the magazine of his split, adding, “and an even better one in two, and an even greater one in five, and it’ll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle.” 

Sudeikis said he was focused on what he could take away from the year.

"That’s an experience that you either learn from or make excuses about,” he said. “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 served custody papers on stage at ComicCon

This seemingly marked the beginning of the end of their friendship. 

An eyewitness attending the event at The Colosseum at Caesars Palace in April 2022 told ET that the actress was introducing the never-before-seen trailer for her and Styles' new movie, Don't Worry Darling, when an unidentified person approached the stage and served her custody papers.

Sudeikis' rep told ET, "Papers were drawn up to establish  jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis." 

The rep added that 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."

When presented with the envelope -- which was marked marked "personal and confidential" -- Wilde asked, "Is this for me?" The eyewitness said the scene was "odd" but "everyone assumed it was something about her presentation," and that Wilde "didn't seem to be shaken" by what had just transpired.

The same eyewitness told ET that Wilde laughed off the seemingly uneventful act, so much so that people attending the event wondered if it was some sort of bit. The manila envelope was never addressed again.

Wilde was served in 'most aggressive manner'

In August 2022, Wilde fired back after she was served custody papers from Sudeikis, according to a new report. In sealed court filings obtained by The Daily Mail, Wilde accused her children's father of malice with the highly public legal move. 

"Jason's actions were clearly intended to threaten me and catch me off guard," Wilde reportedly said in the new documents. "He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible."

She added, "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. 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."

What was said to once be an amicable co-parenting and custody arrangement between the exes has now turned litigious over disagreements regarding where to raise their children.

According to Wilde's motion to dismiss the action from Sudeikis, The Daily Mail reported, the former couple and their children had all been living in London since December 2021. But Sudeikis planned to return to New York City in the summer when he completed work on his Apple TV+ series and hoped to bring the children with him.

"When I did not agree, since the children have not lived in New York for several years, Jason filed these papers," Wilde says, noting that they had initially agreed to send their children back to school in Los Angeles for the upcoming school year. In his own declaration to the court, Sudeikis added that Wilde disclosed to him her plans to move to London at the end of next year. 

"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," Sudeikis claimed. "Second, Olivia said that she intended to relocate with the children to London following the close of school in 2023."

Sudeikis loses custody claim

The Ted Lasso star's custody petition against Wilde was dismissed after a judge ruled that their children's home state is California.

Sudeikis first brought a case against Wilde in New York City family court in October 2021. While he wants to live with the kids in Brooklyn, Wilde would like to be based in Los Angeles and potentially London, where Styles also resides. 

Sudeikis is currently preparing to move back to the U.S. after finishing filming the third and final season of Ted Lasso in the U.K. Now that his initial claim has been dismissed, the case will likely continue in California. Wilde filed a petition to "determine parental relationship in Superior Court of California, in LA," on May 17. 

Wilde reacts to being publicly served papers by Sudeikis

In an Aug. 24 interview with Variety, Wilde didn't hold back about her exact feelings following the events that unfolded at CinemaCon in Las Vegas.

“It was my workplace,” Wilde said. "In any other workplace, it would be seen as an attack. It was really upsetting. It shouldn’t have been able to happen. There was a huge breach in security, which is really scary. The hurdles that you had to jump through to get into that room with several badges, plus special COVID tests that had to be taken days in advance, which gave you wristbands that were necessary to gain access to the event — this was something that required forethought."

She added, "I hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing. To try to sabotage that was really vicious. But I had a job to do; I’m not easily distracted."

That it transpired at all didn't come as a shock to Wilde.

“But, you know, sadly, it was not something that was entirely surprising to me,” she said. “I mean, there’s a reason I left that relationship."

And while the stunt didn't throw her off, Wilde said there were -- and are -- victims in the end.

“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 said. "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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