Looking back! Jason Sudeikis and Olivia Wilde welcomed two children together before splitting in November 2020.
The former couple started dating in 2011 and got engaged two years later. Their son, Otis, and their daughter, Daisy, arrived in 2014 and 2016, respectively.
For the actor, he sees “staying around” was the key to being a great parent to his little ones. “Being present is a good quality,” the Saturday Night Live alum told Us Weekly in April 2018. “At least I’ll know how I screwed them up!”
He went on to joke about the siblings’ dynamic, telling Us, “All Daisy wants to do is play, but playing to her is putting his toys in her mouth. So he gets really mad about that, understandably. When I explained to him that that’s Janet Jackson and Michael Jackson and Janet Jackson is Michael’s younger sister, it’s like of like, ‘Oh, she might be useful!’ He recognizes that, which is good.”
The following year, Wilde exclusively told Us about taking working motherhood “day by day, step by step” so as not to become overwhelmed.
“I think it’s just biting off as much as you can chew, you know, slowly and incrementally,” the filmmaker explained in January 2019. “And I think [it’s] knowing what you’re getting yourself into.”
The New York native added that with so much going on at home and on set, she and the Ted Lasso star had to “prioritize date night.” Wilde gushed at the time: “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. We go to the theater. I love to eat food, so we go to a lot of restaurants, see shows, music — it’s New York! It’s a good thing about living here, live entertainment.”
By November of the following year, Us confirmed that Otis and Daisy’s parents had split, calling off their engagement. The exes “butted heads on many occasions,” a source exclusively told Us in January 2021. “There were arguments and fights over career decisions and where to live.”
The actress moved on with former One Direction member Harry Styles, making their relationship public at his manager’s wedding in January 2021. This “devastated” Sudeikis, the insider said.
Keep scrolling to see the former couple over the years posing for pics with their kids, from red carpet events to playtime at home.