Inside Olivia Wilde & Jason Sudeikis' volatile relationship- as he serves her custody docs while she's speaking on stage

Inside Olivia Wilde & Jason Sudeikis' volatile relationship- as he serves her custody docs while she's speaking on stage


OLIVIA Wilde has just gotten served!

Let's take a look at Olivia and Jason Sudeikis' relationship, what went wrong, and why she got served those custody papers.

When there are two celebrities who are in the spotlight all the time and they decide to date, their names will be in the headlines across the internet.

That's how it has been for Olivia, 38,and Jason, 46, especially the rockier parts.

The couple's relationship started out low-key when they met at a Saturday Night Live after-party.

They were both going through divorces at the time.


Everything to know on Jason Sudeikis and Olivia Wilde’s relationship


Olivia was just getting over her eight-year marriage to Italian filmmaker, Tao Ruspoli.

Jason has just divorced his screenwriter wife, Kay Cannon, whom he was married to for six years.

So, when the actors met at a season 36 SNL after-party for the show's season finale, in May 2011, it was almost like fate.

“I actually came off looking a lot cooler than I really am because I had heard through the grapevine, through mutual friends that weren’t exactly her best girlfriends, that would report back, ‘Oh, you know, I think she’s dating someone,’ so I didn’t make any sort of moves. I was just very, very busy with other things," Jason told Stephen Colbert in 2017.

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But, just six months later, in November of that year, Olivia and Jason began dating.

Olivia told Marie Claire in 2013 that she wasn't exactly looking for love when she met Jason.

"I was just learning to be by myself; I’d been divorced for nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls**t," she said.


The couple had been dating for a year when Jason popped the question in December 2012.

At the time, a source told PEOPLE that the couple was "very, very happy" and were "so excited."

Olivia and Jason did not reveal their engagement to the public until the new year.

In August 2013, the fiances acted together in a movie for the first time.

She played the lead role in Drinking Buddies while Jason had a cameo appearance.


Two months after starring in a movie together, several sources confirmed that Olivia was pregnant with her first child.

She debuted her growing baby bump at the 2014 Oscars in March 2014.

Their first child, Otis, was born on April 20, 2014.

Two years had passed and the couple still had not tied the knot.

Jason joked with Andy Cohen on Watch What Happens Live in April 2016 that they would not get married "until weed was legal in every state."

However, that same month, Olivia confirmed via Instagram that they were expecting their second baby together.

And six months later, on October 11, Daisy Sudeikis was born.


Everything seemed to be going well for the actors.

They weren't married yet, but they were enjoying time with their children.

To have some alone time, Olivia told Us Weekly in 2018 that she and Jason would schedule date nights.

"We prioritize date night. We go out and have a lot of fun. We were both really social people when we met, and we didn’t want to give that up when we became parents, so we’re really consistent about our time with them, but we also prioritize a couple of date nights a week," she told the outlet.

But, even though they made time for themselves, their kids were always first priority.

In March 2018, they made a rare family outing with Otis, 7, and Daisy, 4, at a March For Our Lives event

Posting adorable tributes to each other for Mother's/Father's Day, anniversaries, birthdays, and more, Olivia and Jason seemed happier than ever.

In 2019, Olivia made her directorial debut at the SXSW festival for her film, Booksmart.

Jason stood by her side at the premiere and they were all smiles.

In February 2020, Jason and Olivia took their children to the Harlem Globetrotters game, where they posed for a picture with some of the team members.

The family sat courtside and were both invited to join in at some point during the game.

Little did the public know this would be their last public family outing together.


In 2020, Olivia began filming the movie, Don't Worry, Darling.

The actress directed the film and will also have a small role in it.

Don't Worry, Darling is set to hit theaters this September.

The movie also stars Florence Pugh and Harry Styles in the lead roles.

It was during this time that rumors of Olivia and Jason ending their engagement had started swirling.

In November 2020, news broke that they did break up months prior, but kept it under wraps for months.

The split was amicable and their first priority was their children.

They did not give a reason for their split, but fans had a hunch when she was seen with another celebrity just a few months later.

However, in July 2021, Jason broke his silence about how he felt.

"I'll have a better understanding of why in a year, 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," he told GQ.


It didn't take long for Olivia to move on.

In January 2021, rumors swirled about the Tron: Legacy actress dating Harry Styles, as they stepped out together at his manager's wedding.

After those pictures surfaced, fans thought she cheated on Jason with Harry and that was the reason for their split.

“Olivia called off the engagement in early November but only after she already had gotten close to Harry," an insider told Us Weekly.

"Whether Harry knows it or not, he was a reason for the split and it blindsided Jason," they continued.

However, the source also claimed that the As It Was singer did not break up their engagement.

Olivia and Harry, 28, tend to keep their relationship private but have been seen out together including Coachella, Harry's 2021 tour, and other events where they were papped.

While staying lowkey, Olivia was photographed moving her bags from the house she shared with Jason to Harry's London home.

It didn't take long for engagement rumors to start.

The Instagram gossip account Deuxmoi reported that Harry had popped the question earlier this month.

“I think there is a high probability that they are [engaged]. I’ve been saying for literal months that they are VERY serious and no one ever wants to believe me," their response read.

Neither party has confirmed the rumor, but they both seem to be happy together.


While Olivia moved on, it took Jason a little bit longer.

However, in October 2021, it was confirmed that the Ted Lasso actor was dating model Keeley Hazell after being spotted together in June in New York City.

A source told The Sun, "Jason has always found Keeley incredibly attractive, and has told pals he's had a crush on her since her Page 3 days."

He and Keeley, 35, became pals a few years ago, and stayed in contact, albeit purely platonically.

The couple tends to keep a low profile, except when they are papped.

Neither Jason nor Keeley have confirmed their relationship,


Although it seemed like the two have moved on, they still co-parent their children.

Olivia spoke at the CinemaCon earlier this week to debut a trailer for Don't Worry, Darling, and was handed a mysterious envelope.

The manila envelope was marked "personal and confidential."

“This is for me?” she asked,

She opened the envelope on stage but did not react to what it was and played it coy.

And although Olivia asked if it was a script and appeared unbothered by the awkward exchange, it turned out they were custody papers from Jason.

A spokesperson for Jason told Deadline that he "had no prior knowledge this was going to happen."

He knew the papers had been drawn up but was unaware of where they would be given to his ex and is very displeased with what happened.

Apparently, the custody battle between Olivia and Jason has been messy, according to E! News.

"Their relationship as co-parents is a work in progress. They are figuring it out as they go," an insider told the outlet.

Olivia is very committed to her family, even though she has no intentions of getting back withJason.

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"She wants to make co-parenting work and will do what it takes. She tries just to keep the peace. She knows she is a great mom and will always do what's best for her kids," a source said.

Olivia has not spoken on the subject since she was handed the envelope.

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