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History of Jason Sudeikis’ Relationships: January Jones, Olivia Wilde, and More

Recently, 47-year-old Jason Sudeikis has received attention for reasons other than his acting. The 38-year-old director of Don’t Worry Darling, Olivia Wilde, and the Ted Lasso actor dated for almost ten years before splitting up amid ongoing conflict. Detailed information regarding their relationship, his prior marriage, and his other women is provided below.

Kay Cannon

The Horrible Bosses actor was married to his ex-wife Kay Cannon, 48, from 2004 to 2010, before he started dating Olivia. According to US Weekly, Kay, who was born in Illinois, met Jason in Chicago in the early 2000s. At the Second City, they both performed improv comedy, and by 2004, they were legally wed. After making a significant relocation to New York City, Jason and Kay got married because the 47-year-old had just been offered the job of a lifetime: writing for Saturday Night Live.

Jason was honest with GQ about his marriage and how it ultimately ended in August 2021. “You’re going through a difficult time emotionally and personally, or even professionally if it’s impacting you personally, and then you appear on television for eight minutes while costumed as George Bush. You get a sense of insanity. You experience total insanity. When you catch a glimpse of yourself in the mirror, you may wonder, “Who am I? This is what? Regarding his time on SNL and his marriage ending in 2008, he exclaimed, “Holy hell. Although Kay and the comedian parted ways in 2008, their divorce was not finalized until 2010.

They remain close friends despite their marriage having ended. In February 2021, the Pitch Perfect author gave her ex a heartfelt congratulations on winning the Golden Globe. “In a previous life, @jasonsudeikis and I spent several years watching the #goldenglobes while he was high and sporting a hoodie. Well done, you wanker, on your victory! And congratulations to @TedLasso’s cast and crew. Such a wonderful, humorous, and touching show. Tweeted Kay with the hashtag “believe.”

January Jones

Following their breakup, Jason started dating 44-year-old Mad Men bombshell January Jones. In November 2009, while January was hosting an episode of SNL, the two met, and soon chemistry was evident. They dated from 2010 to 2011, but in the end, the long distance relationship did not work for them. While Jason was based in New York City for the NBC comedy series, the blonde beauty was in Los Angeles filming Mad Men.

“Navigating my first sort of public relationship, with January Jones, was like learning by fire,” he told GQ of their relationship. Which phrase is that? “A test by fire.” Months later, January gave Allure her side of the story, stating that “the long distance kind of petered us out.” “Someone has to make the sacrifices when you date someone who works in the business. If nobody wants to, you just have to be friends.

Olivia Wilde

Ason met Olivia at the Season 36 wrap party in 2011 thanks to his work on Saturday Night Live. When 2013 rolled around, he proposed to Olivia, but they never wed. And after dating for a while, Olivia and Jason had their first child together, Otis, who is now eight years old, before having Daisy, their daughter, in 2016. Sadly, the couple ended their relationship in November 2020, just short of ten years of marriage.

He gave GQ the date of his breakup and admitted that at the time he still wasn’t fully aware of the reasons for it. In one year, two years, and five years, he said, “I’ll have a better grasp of why,” and “it’ll go from being, you know, a book of my life to becoming a chapter, a paragraph, a line, a word, and a doodle.”

Most recently, on October 17, 2022, Olivia and Jason issued a joint statement on allegations made about their breakup by one of their former nannies. “As parents, it is tremendously disheartening to learn that a former nanny of our two young children would chose to make such false and scurrilous charges about us publicly,” said the statement acquired by HollywoodLife.

They said, “Her tragic 18-month campaign of tormenting us, as well as family, close friends, and coworkers, has reached its unfortunate climax. We shall keep putting our efforts into safeguarding and raising our kids in the earnest hope that she will now decide to leave us alone. Since leaving Jason, Olivia has started dating the 28-year-old musician Harry Styles.

Keeley Hazell

Seven months after their breakup, Jason was observed getting close with Keeley Hazell, 36, who played his co-star in the movie Ted Lasso. Then, in November 2021, they were seen kissing once more while on a romantic holiday in Los Cabos, Mexico. According to US Weekly, they were first connected in February 2021, almost seven years after they first met while working on Horrible Bosses 2. According to a source, Jason and the former Page 3 model were initially “just friends,” but by the summer, things had clearly progressed to a love level. Unfortunately, everything nice must eventually come to an end, as the blonde bombshell and Jason decided to call it quits by May 2022, just one year into their relationship.

Are Jason Sudeikis and Keeley Hazell Still Together?

They started dating in February 2021 but broke up permanently in May of this year. She had a brief part in the comedy movie Horrible Bosses 2 in 2014, where the two initially connected. In 2020, Sudeikis cast her as the lead in his popular AppleTV+ series Ted Lasso.

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Who is Jason Sudeikis in a Relationship With?

Here is a detailed timeline of Jason Sudeikis and Olivia Wilde’s relationship, starting with their SNL encounter and ending with their seven-year engagement. All that has been reported is this.


With performances in movies like “Horrible Bosses” and sitcoms like the Emmy-winning “Ted Lasso,” Jason Sudeikis has found success on both the big and small screens. He has amassed a net worth of $25 million from his acting, writing, and producing, according to Celebrity Net Worth.

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