Divorce is messy, but so is a big, public breakup with a longterm ex-fiancé with whom you share two kids. And no one knows this better than Jason Sudeikis and Olivia Wilde, who ended their relationship in 2020 after a seven-year engagement.
Recently, the exes have been duking it out over custody of their children. ICYMI, the couple shares two young kids, a son, Otis, and a daughter, Daisy.
The aftermath of their breakup has been pretty public lately. Olivia was even served with legal papers while she was speaking on stage at CinemaCon in April. But things weren’t always so tense between these two. In fact, they used to be quite the lovebirds. Here’s a look back.
2011: The couple was first linked.
Jason and Olivia first met on the set of Saturday Night Live and hung out at a finale party together. Seems like that's quite the popular place to meet a new boo these days.
“We hit it off that night,” Jason told Stephen Colbert, per People.“I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone.’"
He said he didn't make any moves at first. "I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races," he said.
Apparently, it took him six months to ask her out after they met, per Marie Claire.
"On our first date, in New York City, we closed the restaurant down at 2 a.m.," Olivia told the outlet. "He didn't kiss me, and I was madly in love. I was overwhelmed."
2013: They got engaged
Roughly two years later, Jason asked Olivia to marry him with a 1920s Parisian engagement ring (it had emeralds that encircled a diamond). Olivia told Marie Claire that she later learned Jason had been carrying it around with him for a month.
“Jason has a very trusting way,” Olivia shared at the time. “There is no other way to go through life.”
April 2014: Their first son, Otis, was born.
The couple’s first child, Otis Alexander, was born on April 20, 2014. “Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I’m the building),” Olivia tweeted after his birth.
October 11, 2016: Daisy was born.
Daisy’s birthday coincided with International Day of the Girl, something Olivia pointed out on Instagram. "There goes the neighborhood," she wrote. "Daisy Josephine Sudeikis. Born, like a boss, on #internationaldayofthegirl."
November 2020: Olivia and Jason break up.
The couple—who had been engaged for seven years at this point—finally called it quits in late 2020.
"It's been amicable and they've transitioned into a great co-parenting routine," a source told People. "The children are the priority and the heart of the family's relationship."
Things seemed to be friendly between the exes, and Jason even thanked Olivia at the Critics Choice Awards for her role in shaping his successful series, Ted Lasso.
“I want to thank my kids, Otis and Daisy,” he said. “I want to thank their mom, Otis and Daisy’s mom, Olivia, who had the initial idea for this as a TV show.” Olivia later congratulated Jason on Twitter.
January 2021: Olivia starts dating Harry Styles.
Olivia was spotted holding hands with heartthrob Harry at a wedding, per photos obtained by Page Six. The two met on the set of Olivia’s psychological thriller, Don’t Worry Darling.
April 2022: Olivia was served legal papers at CinemaCon.
Olivia was in the middle of speaking to thousands of film industry executives about her upcoming movie Don't Worry Darling when she was given a manila envelope by a court process server. The moment was captured on video and made its rounds on social media.
Court documents obtained by the Daily Mail detail how Olivia said Jason “clearly meant to threaten” her and wanted to “embarrass” her while she was trying to do her job.
Jason submitted his own filing, per the Daily Mail, saying he didn’t mean for things to unfold the way they did.
"I understand that the process server had only done her job; however, I deeply regret what happened," he said. "Olivia's talk was an important event for Olivia, both professionally and personally, and I am very, very sorry that the incident marred her special moment."
Jason continued, "I did not want service to take place at the home of Olivia's current partner because Otis and Daisy might be present." He also added, "I did not want service to take place at the children's school because parents might be present.”
August 2022: A judge sided with Olivia in the custody battle.
Jason filed a petition that claimed New York as his children’s primary residence. This petition was dismissed by a judge, who determined that the children mostly live in California, per Page Six.
Court documents obtained by Page Six show that Olivia said that the former couple agreed to send their children to school in Los Angeles for the upcoming year as Jason filmed the final season of Ted Lasso in London.
“Recently, however, Jason decided that he wanted to go to New York for the next year while he is not working, and wanted the children to be with him there during this time off,” Olivia wrote. “When I did not agree, since the children have not lived in New York for several years, Jason filed these papers.”
