Cutie pies! Although they ended their engagement in November 2020, Olivia Wilde and Jason Sudeikis welcomed two beautiful children during their relationship.

The actors started dating in 2011 before getting engaged in 2013 and never made it down the aisle, although they lasted through a seven-year engagement. During that time, the Booksmart director and Horrible Bosses star welcomed their two children, Otis, 8, and Daisy, 5. The Life Itself star is now romantically involved with singer Harry Styles.

Olivia shares sweet pictures of her kids on her Instagram account. From visits on set to roaming around the house in costumes, the two kiddos are always as cute as a button.

There goes the neighborhood. Daisy Josephine Sudeikis,” Olivia captioned her October 2016 debut of her newborn daughter. “Born, like a boss, on #internationaldayofthegirl.”

Whenever the three-time Emmy winner is in an interview, he can’t stop gushing over his babies. The We’re the Millers actor joked about how he introduced Otis to video games during lockdown and the child soon became obsessed. However, the now-8-year-old is musically driven. 

“So his birthday is April 20th. He’s a 420 baby and we got him a drum kit” Jason said during a September 2020 interview on The Ellen DeGeneres Show. “But what’s nice is he plays in rhythm one drum at a time. He’s no Dave Grohl quite yet,” he joked. 

The Ted Lasso star hosted Saturday Night Live in October 2021 and couldn’t help but gush over his little ones during his monologue. Jason gave the crowd an update on his life since last hosting the show in 2013, informing them that he is a proud father of two. 

“Great kids, just incredible kids. Um, I don’t know how old they are exactly, so I just don’t pay attention to that kind of stuff; they’re like this and this tall,” he said while placing his hands to the estimated heights of his kids. “But they’re great. You gotta trust me on that.”

However, more than one year after their split in November 2020, she was served custody papers while she was on stage in front of many fans at CinemaCon in May 2022. While the act may have been perceived as insensitive, sources told Us Weekly that Jason was unaware of when the documents were going to be delivered to his ex.

“I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present,” he noted in an August 2022 court filing obtained by the DailyMail

The Don’t Worry Darling filed her own documents as she wanted to raise the children in Los Angeles, whereas Jason wanted them in New York. “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,” she noted in the court filing obtained by the DailyMail. 

The same month, Olivia won a custody battle victory after a judge ruled to keep the case located in California, per her request.

Keep scrolling to see pictures of the adorable kiddos!



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Tyler Cowan