Olivia Wilde and Jason Sudeikis' Relationship Timeline

Olivia Wilde and Jason Sudeikis were together for nine years before splitting ways in 2020: Get the complete story here!

It's been a couple of hard years for Olivia Wilde and Jason Sudeikis amid their drama-filled split and a nasty custody battle. The estranged pair were recently spotted hugging it out in LA, indicating a reformed and amicable friendship between the two. The pair, who were together for nine years, has seemingly called a truce after a year of pointing fingers and throwing accusations against each other. 

 Wilde, 38, is an actress and filmmaker. She is best known for her credits in the television series House, The Lazarus Effect, Booksmart, Tron: Legacy, and the recently released Don't Worry Darling. Her former other half, Sudeikis, 47, is a multi-hyphenated star. Jason is an actor, writer, comedian, and producer. He rose to fame as a sketch writer on Saturday Night Live and later gained recognition for his acting skills in Watching the Detectives, The Ten, Meet Bill, Horrible Bosses, and Ted Lasso.  

Olivia Wilde and Jason Sudeikis' Relationship Timeline!  

From being one of the most adored Hollywood couples to just sharing a relationship as co-parents, Wilde and Jason have come a long and definitely bumpy way. The former pair were engaged for seven years during their nine-year-long relationship. Wilde and Sudeikis's tale started more than 11 years ago at a Saturday Night Live party in 2011. The duo hit it off just right that evening, but it wasn't romance from the get-go. 

"I thought he was so charming. He is a great dancer and I'm a sucker for great dancers. But he didn't even get my number," the Don't Worry Darling star recalls. Both the actress and the writer were reportedly seeing other people, but not exclusively. Despite their instant spark, it took the duo two months to connect. To an eager Olivia, it looked like Jason was intentionally keeping her on the hook, but the Ted Lasso actor had a coherent reason to not make the first move.  

"I had heard through the grapevine, through mutual friends, who would report back, 'Oh you know, I think she's dating someone," Sudeikis said. And when the two eventually started dating in late 2011, things couldn't move faster. By mid-2012, Wilde and Jason were in a live-in relationship and openly gushing about each other. "We hold hands. I never f—— hold hands," Wilde said after announcing she was "blissfully, hopelessly, wildly in love."   

The twosome gradually built a reputation as a low-profile and non-dramatic couple and in January 2013, the smitten pair got engaged. "They are so excited and very, very happy," an insider said after Jason proposed to Wilde with a 1920s Parisian engagement ring.   The pair welcomed their firstborn, Otis Alexander Sudeikis, in April 2014. While the two entering parenthood was an important milestone in their relationship, fans couldn't stop but wonder and speculate about their long engagement.   

Wilde and Sudeikis stood against their former nanny who made false accusations about them!  

Wilde kept asserting a stable and happy relationship but the prying fans' curiosity didn't end. "In many ways, a child is more of a commitment. We are fully committed and really happy as a family," Olivia said.  In another interview, the actress-turned-filmmaker added, "we are seriously connected," Wilde said, adding, "before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it's like, 'Oh, we're committed and promised already."  

The loved-up pair welcomed their daughter Daisy Josephine in October 2016. Wilde and Jason's engagement ended after the two worked in Wilde's 2019 directorial Booksmart. "It's been amicable and they've transitioned into a great co-parenting routine," an insider said about their split.  

Olivia Wilde and Jason Sudeikis Today!  

As fans started to think the two had ended things amicably in November 2020 and that there won't be a nasty side to the story; no one anticipated the drama that was going to follow the aftermath of their breakup. The Booksmart director was the first to move on by dating her Don't Worry Darling co-star Harry Styles in January 2021, following which, close sources reported Sudeikis was still heartbroken.  

"There is still a lot of love there, and he would like to have hope that maybe there's a way for them to repair things," the insider said. Wilde and Styles's new romance gained much media attention amid her fresh split from Sudeikis, but the two kept it low until their breakup in late 2022. During her low-profile romance with the former 1 Direction singer, Wilde and Sudeikis saga continued to make headlines.  

The filmmaker was served legal papers regarding their children's custody while she was at the Cinemacon. Wilde later shared that it was an intentional move by Sudeikis to embarrass her. Sudeikis, on the other hand, casually dated British model Keeley Hazell from early 2021 to May 2022. Wilde was recurringly accused to have cheated on Sudeikis with Styles while she kept refuting the claims. The estranged couple had to stand against their former nanny, who pitched in on the Wilde-Styles-Jason triangle in October 2022.  

"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," the pair's statement read. Before meeting Sudeikis, Wilde dated stars like Justin Timberlake, Ryan Gosling, and director Tai Ruspoli. Sudeikis's romantic history includes names like January Jones and Kay Cannons, with whom he was married from 2004 to 2020. 
 
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