Jason Sudeikis Dating: About His Dating History Unveiled

By Elena Gilbert On Mar 27, 2023

His Breakup with Olivia Wilde and Jason Sudeikis is not seeking a long-term relationship. Yet, the actor was married to writer and director Kay Cannon before he gained notoriety for his romance with Wilde.

Even though their union was short-lived, Sudeikis’ celebrity from his appearances on Saturday Night Live soared during that time. By the time he finished his eight years in the program in 2013, he had already ended his relationship with Cannon and was engaged to Wilde.

Despite having two children together over nine years of marriage, they separated in 2020. Since then, the media has covered their divorce and ensuing custody dispute.

Although Sudeikis has tried to keep the specifics private, he did discuss how the loss of the couple’s relationship had affected him.

“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. 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,” Sudeikis told GQ.

Although they separated in 2022, Sudeikis has since been linked to Keeley Hazell, a castmate from the Ted Lasso movie. Take a peek at Jason Sudeikis’ past relationships below.

Kay Cannon

While performing improv in Chicago in the late 1990s, Sudeikis met author and director Kay Cannon. They married in 2004 after several years of dating.

During their relationship, Sudeikis relocated to New York City and worked as a writer for Saturday Night Live. He subsequently told GQ that he became “unhappy” writing and living apart from his wife, so he asked the show’s creator Lorne Michaels for a role as a cast member.

“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 … ‘ ” Sudeikis said in an interview with GQ in 2011.

In 2008, a few years after Sudeikis joined the cast of the popular program, he and Cannon split. In 2010, their divorce was finalized.

When Cannon congratulated her ex on his Golden Globes victory more than ten years later, she showed that the ex-couple was still on good terms.

“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,” Cannon wrote on Twitter in 2021.

January Jones

Rumors that actor Jason Sudeikis was dating Mad Men actress January Jones began circulating in July 2010. According to reports, the couple got together at an ESPY afterparty and was later photographed on the set of a movie Sudeikis was filming. They were later captured in a photo eating lunch together in Los Angeles.

Later, according to HuffPost, Sudeikis was questioned about the connection while appearing on Lopez Tonight. Although he hesitated to say whether he had seen her “naked and everything,” he affirmed that they were dating.

Although saying he at first “laughed and said, “I do want to get into it! didn’t want to go into it! I have and I do!”

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He’s never seen me naked, and he won’t after those statements, “He’s never seen me naked, nor will he after those comments.” Although she later added, “I think he handled that question very well. He made a joke of it. What was he supposed to say?”

Only a few days later, Sudeikis told Vanity Fair he was “very happy with everything” and that Jones was “great” but sadly, their euphoria didn’t endure long. According to sources, the pair struggled due to the distance and ended their relationship in January 2011 after being “on and off for a few months.”

Olivia Wilde

In May 2011, Sudeikis and Olivia Wilde had their first encounter at a Saturday Night Live after-party. She recalled the Howard Stern Show event: “I was there as someone else’s date.”

“I was seeking this individual, and [Sudeikis] told me I didn’t need to find anything I was looking for. Nonetheless, he protests, saying, “That was true, it wasn’t a line!” Before leaving, Sudeikis remained silent and did not even ask for Wilde’s phone number.

The two frequently ran into each other at gatherings over the following six months, but they could not converse. Eventually, Wilde took matters into her own hands and convinced her closest male friend to provide Sudeikis with her phone number.

In September, the pair went on their first date to a restaurant in New York City. After the date, Wilde declared herself “madly in love.” In November 2011, they started dating.

“They are so excited. … and very, very happy,” a source told PEOPLE during Sudeikis and Wilde’s engagement in 2012. They announced their initial pregnancy in October 2012, and their son Otis Alexander was born six months later.

“In many ways, a child is more of a commitment. We are fully committed and happy as a family,” Wilde told Glamour about wedding plans.

“And there’s no definition of the ‘normal family’ anymore. Kids today are growing up with so many different definitions of family. I guess I’m saying I don’t feel pressured to do it. But I think it will be really fun.”

The engaged couple welcomed their daughter Daisy Josephine as their second child in April 2016. Their family’s “lost member” was discovered the following year when they got Elvis the dog.

Keeley Hazell

Early in 2021, Sudeikis was seen socializing with Keeley Hazell, another cast member of Ted Lasso. According to sources who spoke to PEOPLE, Sudeikis and Hazell first crossed paths on the set of Horrible Bosses 2 when she portrayed Chris Pine’s assistant.

She was spotted wearing the same rainbow tie-dye hoodie that Sudeikis wore during his virtual presence at the Golden Globes that year, not long after the duo was first spotted together at Hazell’s London residence. She even shared an Instagram Story of herself in front of a fireplace resembling the one Sudeikis had in the background of the award event.

Sources claim that even though the couple started to spread dating rumors, Sudeikis wasn’t searching for anything serious at the time. Things seemed to have heated up for the pair by June when they were spotted kissing while visiting New York City, possibly confirming their relationship.

However, they kept their relationship hidden for the rest of that summer, leading some to believe they were again “just friends.” The two weren’t spotted together once more until September when they were captured going on a trek in Los Angeles. They broke up in 2022, though.

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