Photo: Christopher Polk/WireImage ; Noam Galai/Getty
Jason Sudeikisisn’t looking foranything seriousfollowing his split fromOlivia Wilde.
But before the actor made headlines for his relationship with Wilde, he was married to writer and director Kay Cannon. While their marriage only lasted a few years, during that time, Sudeikis skyrocketed to fame thanks to his role onSaturday Night Live. By the time he wrapped his eight-year run on the show in 2013, he had split from Cannon and was newlyengaged to Wilde.
“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 toldGQ.
Since then, Sudeikis has been linked to hisTed LassocastmateKeeley Hazell, although they split in 2022.
Here’s a look at Jason Sudeikis' dating history.
Kay Cannon
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In the late 1990s, Sudeikis met writer and director Kay Cannon while doing improv in Chicago. After dating for several years, they tied the knot in 2004.
During their relationship, Sudeikisaccepted a job as a writeronSaturday Night Liveand moved to New York City. He latertoldGQhe grew “unhappy” living away from his wife and being a writer, so he approached creatorLorne Michaelsfor a job 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 chooseone… ' " Sudeikis said in an interview withGQin 2011.
A few years after becoming a cast member on the hit show, Sudeikis and Cannon separated in 2008. Their divorce was finalized in 2010.
Over a decade later, Cannon proved the former couple were still on good terms when she congratulated her ex on his Golden Globes 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,” Cannonwrote on Twitterin 2021.
January Jones
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In July 2010, Sudeikissparked rumors that he was datingMad Menactress January Jones. The duo were reportedly first spotted coupling up at an ESPY afterparty and were later seen on the set of a movie Sudeikis was filming at the time. Then, they werephotographed togetherwhile grabbing lunch in Los Angeles.
When Sudeikis was later asked about the relationship during an appearance onLopez Tonight, perHuffPost. He confirmed they were dating — although he hesitated to answer whether he had seen her “naked and everything.” Despite initially saying he “didn’t want to get into it,” he jokingly added, “I do want to get into it! I do, and I have!”
Just days later, Sudeikis toldVanity Fairthat Jones was “great” and he was “very happy with everything” — but unfortunately, their happiness didn’t last much longer. Sources told PEOPLE the distance made things difficult between the couple andthey eventually called it quits in January 2011after being “on and off for a few months.”
Olivia Wilde
Sudeikis first met Olivia Wildeduring aSaturday Night Liveafterpartyin May 2011. “I was there as the date of someone else,” she later recalled onThe Howard SternShow. “I was looking for this person, and [Sudeikis] said,‘Whatever you’re looking for, you don’t need it.‘But he claims — he’s like, ‘It was true, it wasn’t a line!’ " Sudeikis didn’t say anything else before walking away — and left without even getting Wilde’s number.
Over the course of the next six months, the duo often bumped into each other at events but still failed to connect. Wilde eventually took matters into her own hands and recruited her best guy friendto give her number to Sudeikis.
The couple had their first date at a restaurant in New York City that fall. By the end of the date, Wilde said she was “madly in love.” They began dating in November 2011.
Sudeikis proposed to Wildeafter the holidays in 2012 and a source told PEOPLE at the time, “They are so excited. … and very, very happy.”
“In many ways, a child is more of a commitment.We are fully committed and really happy as a family,” Wilde toldGlamourwhen asked 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 what I’m saying is that I don’t feel any pressure to do it. But I think it will be really fun.”
The engaged couple welcomed their second child, daughterDaisy Josephinein April 2016. The following year, they found the"missing member” of their broodwhen they adopted their dog, Elvis.
Frazer Harrison/Getty
In November 2020, news broke thatSudeikis and Wilde had ended their engagement. The actresslater revealedthat the couple had “dissolved the relationship towards the beginning of the [COVID-19] pandemic.“Sources told PEOPLEthe split had “been amicable,” and the former couple were making their children “the priority.” Sudeikis and Wilde proved to be on good terms whenthey were spotted embracingjust a few days after their split announcement.
However, their relationship turned when word of Wilde’s relationship withHarry Stylessurfaced early in 2021. At the same time, a source revealed to PEOPLE that Sudeikis was still"absolutely heartbroken” over the breakupand hoped there was a way for the former couple to repair things. Several months later, Sudeikis publicly addressed the split for the first time, sharing that he was trying to learn from the experience.
“That’s an experience that you eitherlearn from or make excuses about. You take some responsibility for it, hold yourself accountable for what you do, and then endeavor to learn something beyond the obvious from it,” he said during an interview withGQ.
In April 2022, details of the former couple’s custody battle were made public whenWilde was served with legal documentsduring an appearance at CinemaCon in Las Vegas. While a source told PEOPLE that Sudeikis “had no prior knowledge” of how the papers would be delivered, Wilde later accused Sudeikis’ actions of being intentional in court documents shefiled to dismisshis petition for custody of their two children.
“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 court filing.
Wildelater spoke out about the situation, saying that trying to “sabotage” the “work of so many different people and the studio” during CinemaCon was “really vicious.” She noted that the incident was “not something that was entirely surprising” to her, admitting there was “a reason [she] left that relationship.”
Amid the legal drama, a source told PEOPLE thatWilde and Sudeikis were no longer speakingand had to have help communicating about their custody schedule. But despite their differences, Wilde recently said that she and Sudeikis have the same intentions regarding their children.
“My priority is them. That’s what it is. It’s as long as they’re happy and they’re healthy then, my ex and I, we agree on that. They are everything to us. There are so many families who are blended. But, you know, it’s tricky because we’re not doing it in private,” Wilde shared.
Keeley Hazell
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In early 2021, Sudeikis wasspotted spending timewith hisTed Lassocastmate Keeley Hazell. Sources told PEOPLE thatSudeikis and Hazell had known “each other from many years ago"after first meeting on the set ofHorrible Bosses 2, where she playedChris Pine’s assistant.
Shortly after the pair were first seen at Hazell’s London home, she was spotted wearing the samerainbow tie-dye hoodiethat Sudeikis wore during his virtual appearance at the Golden Globes that year. She even posted an Instagram Story of herself in front of a fireplace that looked almost identical to the one behind Sudeikis during the award show.
While the couple began to spark dating rumors,sources said Sudeikiswasn’t looking for anything serious at the time. By that June, things appeared to have heated up for the duo as they werespotted coupling upduring a trip to New York City — seemingly confirming their romance. But for the remainder of that summer, they kept things quiet, prompting sources to say they were once again “just friends.” The pair weren’t photographed together again until September, when they wereseen on a hike togetherin Los Angeles.
However, they reportedly split in 2022.
source: people.com
