Jason Sudeikis has had a well-documented romantic history, spanning a marriage, long-term relationships, and rumored flings. The 48-year-old actor, comedian, and writer, best known for his work on Saturday Night Live and Ted Lasso, has kept much of his personal life private. However, his high-profile relationships with Olivia Wilde, January Jones, Kay Cannon, and others have often made headlines.
With a career spanning decades and a net worth of $25 million, Sudeikis has seen both professional and personal ups and downs. His relationships, particularly with Olivia Wilde, have been in the public eye due to their high-profile split and legal battles over custody of their two children. Let’s take a deep dive into Jason Sudeikis’ dating history.
Kay Cannon: Jason Sudeikis’ First Marriage
Sudeikis met writer and director Kay Cannon in the late 1990s while performing improv in Chicago. They quickly formed a connection and dated for several years before tying the knot in 2004. During their marriage, Sudeikis moved to New York City to work as a writer for Saturday Night Live (SNL), a decision that initially created challenges for their relationship.
In a 2011 interview with GQ, Sudeikis recalled how he spoke to SNL creator Lorne Michaels about his struggle with being away from his wife. However, despite efforts to make it work, Sudeikis and Cannon separated in 2008, and their divorce was finalized in 2010.
Despite the breakup, the former couple remained on good terms. In 2021, Cannon congratulated Sudeikis on winning a Golden Globe for Ted Lasso, joking about how she used to watch the show with him when he was “high and wearing a hoodie.”
January Jones: A Short-Lived Romance
Sudeikis moved on from his divorce and was linked to Mad Men actress January Jones in 2010. The two first sparked dating rumors after being spotted together at an ESPY afterparty. They were later seen having lunch in Los Angeles and spending time together on the set of a film Sudeikis was working on.
When asked about their relationship on Lopez Tonight, Sudeikis hesitated before eventually confirming they were dating. However, their romance was short-lived, reportedly due to distance. Sources close to the couple told PEOPLE that they had been “on and off” for a few months before ultimately breaking up in January 2011.
Olivia Wilde: A Decade-Long Relationship
How They Met
Sudeikis met Olivia Wilde at an SNL afterparty in May 2011. At the time, Wilde was with another date, but Sudeikis made a memorable impression with his wit. However, he did not ask for her number. Over the next six months, the two kept running into each other at various events but still failed to connect.
Eventually, Wilde took matters into her own hands and had a friend pass her number to Sudeikis. Their first official date took place later in 2011, and Wilde admitted that by the end of it, she was “madly in love.”
Engagement and Family Life
By the end of 2012, Sudeikis proposed to Wilde, and the couple seemed to be heading towards marriage. They welcomed their first child, Otis Alexander, in 2014, followed by their daughter, Daisy Josephine, in 2016. Despite their deep commitment, they never officially tied the knot.
In interviews, Wilde shared that they felt no pressure to marry, emphasizing their dedication as parents. Their family expanded further in 2017 when they adopted a dog named Elvis.
Breakup and Legal Battle
In November 2020, news broke that Sudeikis and Wilde had ended their engagement after nine years together. Wilde later clarified that the relationship had “dissolved” at the beginning of the COVID-19 pandemic. Initially, their breakup appeared amicable, and they even shared a friendly hug days after the announcement.
However, tensions rose when Wilde started dating Harry Styles in early 2021. Sources close to Sudeikis revealed that he was “heartbroken” and had hoped for reconciliation. By April 2022, their custody battle became public when Wilde was served legal documents while speaking at CinemaCon. Wilde later accused Sudeikis of trying to “embarrass” her, a claim he denied.
Despite their legal issues, Wilde later stated that both she and Sudeikis share the same priorities regarding their children, emphasizing that their focus remains on Otis and Daisy’s well-being.
Keeley Hazell: A Brief Romance
After his split from Wilde, Sudeikis was linked to Keeley Hazell, his Ted Lasso co-star. The two first met years earlier while working on Horrible Bosses 2 in 2014, but their connection deepened in 2021 when they were spotted together in London.
Fans speculated about their relationship when Hazell was seen wearing the same tie-dye hoodie Sudeikis had worn during a virtual Golden Globes appearance. That summer, they were seen in New York City, seemingly confirming their romance. However, by the end of 2021, sources indicated they had cooled off and were “just friends.” They were spotted together one final time on a hike in Los Angeles in 2022, but they reportedly split soon after.
Jason Sudeikis Today: Prioritizing Family and Career
As of 2024, Jason Sudeikis is not publicly dating anyone. While he keeps his romantic life private, sources say he is focused on co-parenting his children and continuing his successful career. His critically acclaimed series, Ted Lasso, has cemented his status as one of television’s most beloved stars.
Though his relationships have been in the spotlight, Sudeikis has consistently handled them with humor, grace, and maturity. Whether or not he finds a new romance, his legacy as a talented comedian, dedicated father, and respected actor remains stronger than ever.
