When Olivia Wilde and Jason Sudeikis started dating in 2011, everyone around them agreed they were a perfect match—they were both renowned Hollywood elites who had been previously married. The former, an American actress and filmmaker, was married to Italian-American filmmaker Tao Ruspoli from 2003 to 2011. The American actor and comedian, on the other hand, was married to Kay Cannon from 2004 to 2010. Their divorce experience and understanding of Hollywood were imagined as an advantage for an enduring romance, but it didn’t get them up to a decade together.
Jason Sudeikis has been reluctant to jump back into the dating pool since his split from Olivia Wilde, but the Rush actress was quick to find another partner. She began dating English singer and actor Harry Styles in January 2021, after they met in late 2020 while filming her psychological thriller Don’t Worry Darling. While there have been claims that Wilde left Sudeikis for Styles, she has maintained that her relationship with the comedian was long over before Styles came into the picture. Wilde and Styles broke up in November 2022, and here’s a rundown of what transpired between her and Sudeikis.
Olivia Wilde And Jason Sudeikis Met At Party In May 2011
Their love story began at a Saturday Night Live finale party in May 2011. While their encounter didn’t lead to an instant relationship, they kept running into each other and ultimately had their first date. Recalling how they met, Olivia Wilde disclosed that she was immediately attracted to him. “I met Jason, and I thought he was so charming,” she told Allure. “He’s a great dancer, and I’m a sucker for great dancers,” added the actress. Sudeikis was also attracted to Wilde the night they met. He revealed in April 2017 on The Late Show with Stephen Colbert that they were drawn to each other when they met. “We hit it off that night,” he said.
However, it took the comedian six months to get Wilde’s phone number and another month before he texted her. “…My best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning,” the actress divulged. Despite getting her number, Sudeikis didn’t text Olivia until a month later. He told Colbert he stalled because Olivia’s friends said she was dating someone. “I actually came off looking a little cooler than I really am because I had heard…through mutual friends who weren’t exactly her best girlfriends… (that) she’s dating someone,” explained the Saturday Night Live alum.
They Began Dating In November 2011 And Got Engaged In January 2013
When Jason Sudeikis eventually reached out to Olivia Wilde for their first date, she felt insecure about going out with him. She thought he was too cool and funny to be interested in her. “I thought, ‘He won’t be interested in me; I’m not a contender,'” she told Marie Clarie in March 2013. Jason also delayed their first kiss until their fourth date. “He literally didn’t kiss me until the fourth date,” Wilde told Howard Stern in a March 2016 interview, adding that she was “completely head over heels” when he eventually did,
Fast forward to October 2012 and the two were already living together. Olivia Wilde moved from Los Angeles to Manhattan, New York, to live with Jason Sudeikis. She told USA Today it was a good life. “I’ve been decorating our new apartment…We have a cool new electronic drum kit. It’s a good life. For years, I worked constantly. I was doing the show (House) and doing movies on the weekends,” she said. The former couple got engaged in January 2013 after Sudeikis proposed with a Parisian diamond-emerald ring. Unfortunately, they didn’t get to exchange marital vows.
Breakup And Child Custody Battle
Olivia Wilde and Jason Sudeikis called off their engagement in November 2020. Sources close to them have insisted they had no scandal but simply drifted apart. However, it has been suggested in some quarters that Wilde left Sudeikis for Harry Styles. The House actress denied and dismissed the rumor in an interview with Vanity Fair. “The complete horses**t idea that I left Jason for Harry is completely inaccurate,” she told the publication. They had two kids before their breakup: Otis Alexander, born in 2014, and Daisy Josephine, born in 2016. The exes were embroiled in a painful legal battle over the custody of their children after calling off their engagement.
Wilde was served legal papers in April 2022 while onstage at CinemaCon. Although Sudeikis’ representative said he wasn’t aware she would be served in public, the actress told Variety it was a vicious move. “It was really upsetting,” she said, “It shouldn’t have been able to happen. There was a huge breach in security, which is really scary,” she added. Apart from the amount to be designated for the upkeep of their children, the exes were at loggerheads over where the kids should live. While Olivia wanted them to live in Los Angeles and London, where Harry Styles was based, Jason legally asked for New York City to be Otis and Daisy’s custody base.
Olivia Wilde And Jason Sudeikis Resolved Their Custody Battle In September 2023
The custody battle lingered for nearly two years before Wilde and Sudeikis settled. They privately resolved their differences over the issue in September 2023, with the comedian accepting to pay $27,500 monthly in child support. Legal documents disclosed he agreed to pay $10,300 for Otis and $17,200 for Daisy. In addition to that, he consented to cover 25 percent of Wilde’s childcare expenses. Sudeikis lost his quest to have the kids’ custody based in New York City and settled for a week-on, week-off custody schedule. The exes have maintained a cordial relationship for the sake of their children, but their fallout has probably ruined any chance of collaborating on any project.
While they were dating, Olivia Wilde and Jason Sudeikis worked together in Joe Swanberg’s Drinking Buddies (2013), Matthew Akers’ David Blaine: Real or Magic (2013), and Booksmart, a 2019 comedy film directed by Wilde, wherein Sudeikis played Principal Jordan Brown. The comedian co-created and began starring as the titular character in Apple TV+’s Ted Lasso in 2020. He publicly gave his former fiancée credit in March 2021 for coming up with the idea that turned Ted Lasso into a show. After the sports comedy-drama television series won him the Critics Choice Award for Best Comedy Series, he thanked “Mom Olivia, who had the initial idea to do this as a TV show…” It remains to be seen where their relationship goes from here.
