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Jason Sudeikis and Olivia Wilde’s Relationship Timeline: From Engagement, Kids to Harry Styles Romance

Jason Sudeikis and Olivia Wilde seemed like Hollywood’s more perfect — and fun-loving  — couple. They spent nine years together, the last seven of which they were engaged, and had two beautiful children. But after their sudden split followed by her romance with Harry Styles, things got complicated

The actress-turned-director was presenting a clip reel of footage from her highly anticipated new film, Don’t Worry Darling, at CinemaCon in Las Vegas on April 26, 2022, when a process server presented her with a manila envelope containing child custody papers from Jason while she was onstage. Olivia took a quick look at the contents, maintained her cool and went on with the presentation of the movie, which stars her former boyfriend Harry.

In a statement provided to Deadline, Jason’s spokesperson said the actor “had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved.” At the time, the Emmy winner was in London shooting the upcoming season of Ted Lasso.

The couple began dating in 2011 after meeting at the season 36 Saturday Night Live season wrap afterparty. Both were coming off divorces at the time. Olivia told Marie Claire in 2013 that she felt an immediate connection with Jason. “I was just learning to be by myself. I’d been divorced nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls–t.”

The pair became engaged over the holidays in 2012, revealing the news in early 2013. That same year, Jason appeared in Olivia’s film Drinking Buddies. But the biggest news of 2013 was when the couple found out they were expecting their first child together.

Jason Sudeikis and Olivia Wilde Relationship Timeline
Gregory Pace/Shutterstock

Their son, Otis, arrived in April 2014. He got a little sister when the couple welcomed daughter Daisy Josephine in October 2016. While the couple were still in no rush to marry, Olivia professed her love for her partner in a 2017 Instagram tribute celebrating Jason’s 42nd birthday.

She wrote, “I have approximately one billion pictures of this guy, my partner in life-crime, who was born on this day in 1975. But this one represents his latest chapter, the one in which he became a dad to a little woman, who will grow up thinking all men can dance, sink a jump shot, and tell great jokes,” next to a photo of Jason and Daisy playing together. “Oh well. Happpppppy Birthdayyyyyyyyy, Jason. I love you!” Olivia gushed.

The pair continued to show their love and support for each other’s careers, attending red carpet premieres and events together. Jason even accompanied Olivia to the premiere of her directorial debut, Booksmart, at the SXSW Festival in 2019.

The couple stunned fans by calling off their nine-year relationship in November 2020. The mystery surrounding the breakup became a little clearer when on January 4, 2021, Olivia was photographed openly holding hands with the former One Direction singer, whom she directed in her second film, Don’t Worry Darling, which had just wrapped shooting. Olivia moved her belongings out of the home she shared with Jason and into Harry’s a month later on Valentine’s Day.

Jason later told GQ in August 2021 about how he was still trying to process the split and Olivia’s immediate new romance. “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 explained.

Scroll down for Jason and Olivia’s relationship timeline in photos.