Everything Olivia Wilde and Jason Sudeikis Have Said About Their Relationship Over the Years

Credit: Evan Agostini/Invision/AP/Shutterstock

Everything Olivia Wilde and Jason Sudeikis Have Said About Their Relationship Over the Years

The way they were. Before Jason Sudeikis and Olivia Wilde split, they weren't afraid to gush about their love for each other. The duo met in May 2011 at a wrap party for the season 36 finale of Saturday Night Live, but they didn't start dating for another six months. Both had already been married once, and the Booksmart director later said that was one reason she decided to take it slow. “I was just learning to be by myself; I’d been divorced nine months," the O.C. alum told Marie Claire in March 2013. "We were both seeing people but were single. He seemed to really see me, see through the bulls–t.” The Drinking Buddies star filed for divorce from Tao Ruspoli in March 2011 after nearly eight years of marriage. Sudeikis, for his part, was married to SNL writer Kay Cannon from 2004 to 2010. The Emmy winner also wanted to take his time with Wilde because he knew immediately that she was special. “I just had a hunch that the second I kissed her, I wasn’t going to end up kissing ever kissing anyone ever again,” he told Access Hollywood in August 2020. “So, it was like I had to be careful with it.” [jwplayer AlQBVIda-zhNYySv2] While Wilde's first marriage ended in divorce, she still felt that it helped prepare for her next serious relationship. “I’m so grateful for the pain and the heartbreak," she told Marie Claire in the same interview. "It gave me the courage to leave and brought me to the great love of my life.” The Horrible Bosses actor and the House alum announced their engagement in 2013 after two years together. In April 2014, the duo welcomed son Otis, while daughter Daisy followed in October 2016. After the arrival of Otis, Wilde said that she felt children represented a more powerful commitment than a marriage certificate. “We are seriously connected,” she told Net-a-Porter’s Porter Edit in February 2016. “Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it’s like, ‘Oh, we’re committed and promised already.’” In November 2020, however, the pair split after nearly a decade together. Wilde moved on with Harry Styles, whom she connected with while directing him in her upcoming film Don't Worry Darling. After the film wrapped, the Rush actress praised his performance in a lengthy Instagram post. "He infused every scene with a nuanced sense of humanity," she wrote in February 2021. "He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards." Sudeikis, meanwhile, has been linked to Keeley Hazell, who has appeared on Ted Lasso, since June 2021. The SNL alum and the model have kept their romance relatively private, but in November 2021, they were spotted packing on the PDA during a trip to Mexico. Keep scrolling to see what Sudeikis and Wilde have said about each other over the years. [podcast_block]

Credit: Evan Agostini/Invision/AP/Shutterstock

Everything Olivia Wilde and Jason Sudeikis Have Said About Their Relationship Over the Years

The way they were. Before Jason Sudeikis and Olivia Wilde split, they weren't afraid to gush about their love for each other. The duo met in May 2011 at a wrap party for the season 36 finale of Saturday Night Live, but they didn't start dating for another six months. Both had already been married once, and the Booksmart director later said that was one reason she decided to take it slow. “I was just learning to be by myself; I’d been divorced nine months," the O.C. alum told Marie Claire in March 2013. "We were both seeing people but were single. He seemed to really see me, see through the bulls–t.” The Drinking Buddies star filed for divorce from Tao Ruspoli in March 2011 after nearly eight years of marriage. Sudeikis, for his part, was married to SNL writer Kay Cannon from 2004 to 2010. The Emmy winner also wanted to take his time with Wilde because he knew immediately that she was special. “I just had a hunch that the second I kissed her, I wasn’t going to end up kissing ever kissing anyone ever again,” he told Access Hollywood in August 2020. “So, it was like I had to be careful with it.” [jwplayer AlQBVIda-zhNYySv2] While Wilde's first marriage ended in divorce, she still felt that it helped prepare for her next serious relationship. “I’m so grateful for the pain and the heartbreak," she told Marie Claire in the same interview. "It gave me the courage to leave and brought me to the great love of my life.” The Horrible Bosses actor and the House alum announced their engagement in 2013 after two years together. In April 2014, the duo welcomed son Otis, while daughter Daisy followed in October 2016. After the arrival of Otis, Wilde said that she felt children represented a more powerful commitment than a marriage certificate. “We are seriously connected,” she told Net-a-Porter’s Porter Edit in February 2016. “Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it’s like, ‘Oh, we’re committed and promised already.’” In November 2020, however, the pair split after nearly a decade together. Wilde moved on with Harry Styles, whom she connected with while directing him in her upcoming film Don't Worry Darling. After the film wrapped, the Rush actress praised his performance in a lengthy Instagram post. "He infused every scene with a nuanced sense of humanity," she wrote in February 2021. "He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards." Sudeikis, meanwhile, has been linked to Keeley Hazell, who has appeared on Ted Lasso, since June 2021. The SNL alum and the model have kept their romance relatively private, but in November 2021, they were spotted packing on the PDA during a trip to Mexico. Keep scrolling to see what Sudeikis and Wilde have said about each other over the years. [podcast_block]

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The Marathon Thing

In October 2012, Wilde made headlines when she gave a very candid quote about the couple's sex life. "[We] have sex like Kenyan marathon runners," she said while giving a monologue at These Girls, hosted by Glamour. She added that she was “blissfully, hopefully, wildly in love” with Sudeikis.

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What She Loved

"He was so handsome, and he could dance," Wilde told Marie Claire of her then-fiancé in March 2013. "He’s so good with kids. ... I’ve never before experienced looking at someone and thinking, 'That’s who I want to raise a child with.'”

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What He Loved

"[Olivia] is a combination of everything that I love about women — she's smart, strong, caring, beautiful and as funny as anybody I've ever known," Sudeikis gushed to InStyle in July 2013. "She just has it all. It's like she's the most gorgeous Costco you've ever seen in your life. Early on in our relationship, I would sneak onto her Twitter and read through things she had written. I'd be like, 'This is awesome. She's awesome.'"

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Good With Kids

"Jason is fantastic with children," Wilde told Allure of Sudeikis in September 2013. She also said the couple were working on wedding planning at the time. "I trust everyone to not leak any information," she explained, adding that it would be a "funny, silly" event. "I just hope no one ends up flying a stupid helicopter over it or anything dumb like that."

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He's Got Moves

“I met Jason, and I thought he was so charming,” the In Time star told Allure in September 2013. “He’s a great dancer and I’m a sucker for great dancers. But he didn’t even get my number. Over the next six months, we kept running into each other. [One night] my best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning.”

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Taking It Slow

During a March 2016 interview with Howard Stern, Wilde recalled how Sudeikis charmed her right away when they met in 2011. “I was on the dance floor and everybody was dancing around me and they seemed really happy, and I was just kind of standing there,” she said. The comedian then walked up to her and said, “Whatever you’re looking for, you don’t need it.” He got her number, but he waited a full month to send her a message. “I was on the hook,” she joked. “I was like, ‘Did Jason Sudeikis die? Because I don’t have any texts.’”

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Low Pressure

The We're the Millers star shared his side of the first meeting story during an April 2017 appearance on The Late Show With Stephen Colbert. “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 explained. “So, I didn’t make any moves. 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. ”

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The Importance of Alone Time

“We prioritize date night,” the Life Itself actress exclusively told Us Weekly in February 2019, explaining how she and Sudeikis kept their romance alive. “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.”

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Working Together

In May 2019, Wilde gushed about how much fun it was to work with Sudeikis on her movie Booksmart. "There's still a shorthand that comes from being someone's closest partner, but I loved being able to just set him free, because he's one of the best improvisers in the world," she told Entertainment Tonight at the time. "And I just loved that we got him to take this bit of information that we had in the script and run with it."

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Moving On

Sudeikis opened up about his split from Wilde for the first time in July 2021. “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 told GQ at the time, noting that he'd hit "rock bottom" in the previous year. “That's an experience that you either learn from or make excuses about. You take some responsibility for it, hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it.” 

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Public Embarrassment?

After Sudeikis publicly served Wilde with custody papers in April 2022, she filed her own documents several months later.

“Jason’s actions were clearly intended to threaten me and catch me off guard. He could have served me discreetly, but instead, he chose to serve me in the most aggressive manner possible,” Wilde claimed in her August 2022 filing, obtained by the Daily Mail. “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. Since Jason has made it clear that we will not be able to work this out for our children’s sake outside of the court system, I filed a petition for custody in Los Angeles.”

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Choosing How to Serve Custody Papers

While the House alum alleged that Sudeikis served her during her CinemaCon appearance in a quest to embarrass her, the Mother’s Day actor responded in his own August 2022 court docs.

“I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present,” Sudeikis reportedly wrote, referring to Wilde’s boyfriend, Harry Styles. “I did not want service to take place at the children’s school because parents might be present.”

He added: “I understand that the process server had only done her job; however, I deeply regret what happened. 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.”

Sudeikis further alleged that Wilde told him that he could only “spend time” with Otis and Daisy on weekends and during vacations if he did not live in Los Angeles full-time. The Kansas native — who’s been filming Ted Lasso in London — alleged that would deprive him of his “right to parent the children during important periods of their lives.”

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Custody 'Nastiness'

Months after she was served with legal documents while on stage at CinemaCon in Las Vegas, Wilde reflected on the "attack" during an August 2022 Variety interview. "I hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing," she said. "To try to sabotage that was really vicious. But I had a job to do; I'm not easily distracted. But, you know, sadly, it was not something that was entirely surprising to me. I mean, there's a reason I left that relationship."

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The Way It Ended

In a Vanity Fair cover story, Wilde slammed the notion that she had “left Jason for Harry,” which she called a “complete horses—t idea.”

“[It] is completely inaccurate,” Wilde said in a September 2022 profile. “Our relationship was over long before I met Harry. Like any relationship that ends, it doesn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic. We were raising two kids during lockdown, so we coparented through that time.”

She continued: “Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to not because we could be better parents as friends who live in different houses.”

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Slamming the Nanny

After the former couple's nanny spoke to the Daily Mail in October 2022 and made several accusations about their split — including that Wilde cheated on Sudeikis with Styles and the SNL alum laid himself under her car to stop her from going to visit the "Little Freak" singer — the actors put a stop to the drama with a rare, joint statement.

“As parents, it’s incredibly upsetting to learn that a former nanny of our two young children would choose to make up such false and scurrilous accusations about us publicly,” Wilde and Sudeikis told Us Weekly. “This is the unfortunate apex of a now, 18-month-long campaign of harassing us, as well as our loved ones, close friends and colleagues. We will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone.”