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With such a high-profile separation from Olivia Wilde that was rumored to have stemmed from a cheating scandal concerning Harry Styles—though that’s been repeatedly denied—the question of who is Jason Sudeikis dating now is always a hot topic of conversation.
The Ted Lasso creator and star’s love life dominated the news cycle in 2021 and 2022 when he split from Wilde after nine years together, a seven-year engagement, and two children: Otis born in 2014 and Daisy born in 2016. “I’ll have a better understanding of why [it happened] in a year,” he said of their split in an interview with GQ in 2021. “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 continued, “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.”
Who is Jason Sudeikis dating now?
Who is Jason Sudeikis dating now? The comedy writer is reportedly single as of March 2023 though he was romantically involved with a Ted Lasso co-star. More on that below.
Keely Hazell: 2021 – 2022
Sudeikis was confirmed to be dating Keely Hazell for about a year. Hazell plays Bex in the hit AppleTV+ series Ted Lasso, the third season of which debuted on the streaming platform on March 15, 2023.
A source told The Sun in May 2022 that, “Jason has always found Keeley incredibly attractive and has told pals he’s had a crush on her since her Page 3 days,” and they had been friends since they met on the set of Horrible Bosses 2. They were linked in February 2021 and were photographed a few months later getting intimate on an afternoon stroll around NYC. But after a year together, they’d split. A source told E! News in July 2021 that the father-of-two and actress were “no longer romantic” after enjoying a brief relationship. “Jason and Keeley were never in a serious relationship,” they said. “It was definitely never a serious thing.” At the Ted Lasso season three premiere in LA on March 7, 2023, Sudeikis and Hazell kept their distance.
Olivia Wilde: 2011 – 2020
Sudeikis and Wilde met at a finale party for Saturday Night Live in 2011 and they “hit it off”, as Sudeikis described in an interview with Stephen Colbert in 2017. They went on their first date later that year, but they didn’t kiss until the fourth date, Wilde told Howard Stern in March 2016. “He finally kissed me and I was like, completely head over heels.” In January 2013, Sudeikis proposed and by October, Wilde was pregnant with their first child, Otis.
After Otis was born, Wilde told Glamour in August 2014 that the couple was in no rush to tie the knot and they were just enjoying being parents. “In many ways, a child is more of a commitment. We are fully committed and really happy as a family,” she shared. “And there’s no definition of the ‘normal family’ anymore. Kids today are growing up with so many different definitions of family. I guess what I’m saying is that I don’t feel any pressure to do it. But I think it will be really fun.” In April 2016, Wilde announced she was pregnant with their second child, daughter Daisy and the couple welcomed her in October of that year.
Four years later, People reported in November 2020 that Wilde and Sudeikis had called off their engagement. “It’s been amicable and they’ve transitioned into a great co-parenting routine,” a source said. “The children are the priority and the heart of the family’s relationship.”
In January 2021, Wilde was spotted holding hands with Harry Styles after they met on the set of Wilde’s film, Don’t Worry Darling. A source told People Sudeikis was “heartbroken” and that “he would like to have hope that maybe there’s a way for them to repair things.”
Wilde confirmed the relationship running its course in an interview with Vanity Fair in September 2022 but denied she had cheated on Sudeikis with Styles. “The complete horses— idea that I left Jason for Harry is completely inaccurate,” said Wilde. “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.”
“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,” she said of her custody battle of their kids. “I evolved a lot between when I was 27 and 35. I found myself as a director. And I think I found myself as an individual. And sometimes when you evolve, you evolve out of relationships that were based on an earlier version of yourself.”
While on stage presenting Don’t Worry Darling in front of 3,000 audience members at CinemaCon in Las Vegas on April 27, 2022, Wilde was interrupted by a woman to give her a manila envelope labeled “Personal and Confidential.” “This is for me?” Wilde questioned, commenting about how the envelope was “very mysterious” before telling the crowd that she was “going to open it now because it feels like it’s a script.” When she opened the envelope and saw they were custody papers from Sudeikis, Wilde put the papers back in the envelope and said, “OK, got it. Thank you.” She continued her presentation on Don’t Worry Darling and didn’t talk about the envelope again.
In court documents obtained by Us Weekly on August 10, 2022, Jason wrote: “I did not want service to take place at the home of Olivia’s current partner because Otis and Daisy might be present,” referring to Styles at the time. “I did not want service to take place at the children’s school because parents might be present.” Sudeikis then apologized to Wilde for ruining her talk. “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.”
Weeks after the Tron: Legacy star reflected on the moment and how it was inappropriate. “To try to sabotage that was really vicious. But I had a job to do; I’m not easily distracted,” she told Variety in late August 2022. “But, you know, sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship.”
January Jones: 2010 – 2011
In July 2010, Sudeikis and Mad Men star January Jones sparked dating rumors when they were spotted coupling up at an ESPY afterparty. He confirmed to HuffPost that they were dating and when asked whether he had seen her “naked and everything,” Jason first said, “I don’t want to get into it.” Then: “I’m kidding. I do want to get into it! I do, and I have!”
Kay Cannon: 2004 – 2010
Sudeikis met writer and director Kay Cannon while doing improv in Chicago. They dated for a few years and tied the knot in 2004. During their relationship, he was offered a job as a writer on SNL but he was “unhappy” living away from his wife and being a writer. He needed something more.
In an interview with GQ: “He had the best line. I go, ‘I had to give up two things I love the most to take this writing job: performing and living with my wife.’ And on a dime, he just goes, ‘Well, if you had to choose one’,”. But time apart must’ve impacted the couple because they separated in 2008 and finalized their divorce in 2010.
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