Jason Sudeikis’ Girlfriend: Meet His Ex Olivia Wilde & More – Hollywood Life

Jason Sudeikis’ Girlfriend: Everything To Know About Ex Olivia Wilde & His Dating History

Jason Sudeikis may be one of Hollywood's most funny actors, but did you know he was once married? Here is everything to know about his exes, including 'Don't Worry Darling' director, Olivia Wilde.

Reading Time: 5 minutes
View gallery
Image Credit: Evan Agostini/Invision/AP/Shutterstock

  • Jason Sudeikis is an actor from Virginia who is most known for his role on the hit Apple TV+ series, Ted Lasso.
  • He is currently single, but he was previously married to Kay Cannon.
  • The We’re the Millers star also dated actresses Olivia Wilde and January Jones.
  • Jason is currently on location in the UK filming Season 3 of Ted Lasso.

Jason Sudeikis, 47, has recently been in the spotlight for more than just his acting. The Ted Lasso star was in a long-term relationship with Don’t Worry Darling director, Olivia Wilde, 38, for almost a decade and the two have had continuous drama since their split. Here is everything you need to know about their relationship, his previous marriage, and his other ladies below!

‘Pitch Perfect’ screenwriter, Kay Cannon, was married to Jason from 2004 to 2010. (Ron Eshel/Invision/AP/Shutterstock)

His Ex-Wife, Kay Cannon

Before dating Olivia, the Horrible Bosses actor was married to his ex, Kay Cannon, 48, from 2004 to 2010. Kay, who was born in the state of Illinois, met Jason in Chicago during the early 2000s, per US Weekly. Both of them were doing improv comedy at the Second City, and by 2004 they were officially husband and wife. Jason and Kay got married following their big move to New York City, as the 47-year-old has just landed the job of a lifetime – writing for Saturday Night Live.

In Aug. 2021, Jason opened up to GQ about his marriage and how it ultimately unraveled. “You’re going through something emotionally and personally, or even professionally if that’s affecting you personally, and then you’re dressed up like George Bush and you’re live on television for eight minutes. You feel like a crazy person. You feel absolutely crazy. You’re looking at yourself in the mirror and you’re just like, ‘Who am I? What is this? Holy hell,'” he said of his time on SNL and his marriage ending in 2008. Kay and the funnyman split in 2008 but were not officially divorced until 2010.

Despite the end of their marriage, they are still good friends. The Pitch Perfect screenwriter gave her ex a loving shoutout in Feb. 2021 for his Golden Globe win. “A lifetime ago, I spent several years watching the #goldenglobes w/ @jasonsudeikis while he was high & wearing a hoodie. Congrats on your win, ya wanker! And congrats to the cast & crew of @TedLasso . Such a great, funny & heartfelt show. #believe,” Kay wrote via Twitter.

January Jones

After his split from Kay, Jason then went on to date Mad Men bombshell January Jones, 44. The pair met while January was hosting an episode of SNL in Nov. 2009, and soon sparks were flying. While they dated from 2010 to 2011, in the end, they could not make the long distance relationship work. The blonde beauty was in Los Angeles filming Mad Men while Jason was based in NYC for the NBC comedy show.

He recalled his relationship with her to GQ, “navigating my first sort of public relationship, with January Jones, which was like learning by fire. What is the term? Trial by fire.” And just months after their breakup, January told Allure her side of the story, “the long distance kind of petered us out,” she said. “When you date someone else who’s in the industry, someone has to make the sacrifices. And if no one’s willing to, then you just have to be friends.”

Olivia Wilde

jason sudeikis & olivia
Olivia Wilde & Jason Sudeikis were together from 2011 until 2020. (Evan Agostini/Invision/AP/Shutterstock)

Jason’s time on SNL brought him more than one love, as he eventually met Olivia at the Season 36 wrap party in 2011. By 2013, he asked Olivia to marry him, but they never actually got married. And after a few years of dating, Olivia and Jason welcomed their first child together, Otis, 8, before their daughter, Daisy, 6, was born in 2016. But sadly, the pair called it quits in November 2020, just shy of completing a decade together.

He confirmed the date of his split to GQ and told the outlet he still hadn’t quite understood the reasons of the break up at the time. “I’ll have a better understanding of why in a year,” he said, “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.”

Most recently, on Oct. 17, 2022, Olivia and Jason released a joint statement about one of their former nannies’ claims about their breakup. The statement obtained by HollywoodLife read, “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly.”

“Her now 18 month long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex,” they added. “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.“ Olivia has since moved on from Jason and is dating musician Harry Styles, 28.

Keeley Hazell

Seven months after Jason’s split from the Booksmart director, he was spotted packing on the PDA with his Ted Lasso costar, Keeley Hazell, 36. They were then spotted kissing once more during a romantic getaway in Los Cabos, Mexico, in Nov. 2021. They were initially linked to each other in Feb. 2021, about seven years after they had met while filming Horrible Bosses 2 together, per US Weekly. A source told the outlet that at the time Jason and the former Page 3 model were “just friends” but clearly things got romantic by that summer. Sadly, all good things sometimes come to an end, as the blonde bombshell and Jason called it quits by May 2022, just after one year together.