Olivia and the Saturday Night Live alum first sparked romance rumors in 2011 after meeting at an SNL wrap party in May of that year.
“I met her at a finale party for SNL,” the Horrible Bosses star told Stephen Colbert of their chance encounter during a 2017 appearance on The Late Show With Stephen Colbert. “We hit it off that night.”
As for The O.C. alum, she told Allure that it was Jason’s dance moves that caught her attention. “I met Jason, and I thought he was so charming. He’s a great dancer, and I’m a sucker for great dancers. But he didn’t even get my number,” she said during a September 2013 interview.
Jason popped the question and the two got engaged in January 2013.
“We’ve discussed all our ideals and hopes. I can’t wait for children. I’m open-minded about how many, but three, which I love, is like a little party. I am not trying to have kids now — there’s no strict plan for anything in my life. What happens, happens. He’s so good with kids,” Olivia told Marie Claire in March of that year. “I’ve never before experienced looking at someone and thinking, ‘That’s who I want to raise a child with,’” she added.
Despite not having a timeline for their wedding or children, Jason and Olivia announced they were expecting their first child together that October. “They are incredibly happy,” the couple’s reps told People. “They’re very excited to welcome a new member into their family.”
On April 20, 2014, Olivia gave birth to a baby boy. “Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I’m the building),” she announced via Twitter days after his arrival.
Two years later, just two days ahead of Otis’ second birthday, the New York native shared a photo of herself rocking a pregnant belly.
“Matching baby bumps,” she captioned her April 2016 Instagram post, adding a peace sign emoji, alongside a black and white photo of herself and Otis holding their exposed stomachs.
Daughter Daisy Josephine Sudeikis joined the family on October 11, 2016. “There goes the neighborhood … Born, like a boss, on [International Day of the Girl],” the mother of two captioned their birth announcement.
“The split happened at the beginning of the year,” a source close to the duo told the outlet. “It’s been amicable, and they’ve transitioned into a great coparenting routine. The children are the priority and the heart of the family’s relationship.”
Though the former couple never made it down the aisle, they continue to battle over custody of their son and daughter.
Keep scrolling for the latest on their ongoing legal drama over their children.