Jason Sudeikis’ Wife: Meet ‘Ted Lasso’ Star’s Exes Kay Cannon, Olivia Wilde, & Who He’s Dating Now

Jason Sudeikis was married once and dated various women over the years. Find out more about his romantic past here.

• Jason Sudeikis is best known as an actor.
• He is currently not married and not known to be dating anyone.
• He was previously married to Kay Cannon and had romances with Olivia Wilde and more.
• Jason recently attended the premiere for his show ‘Ted Lasso’ and one of his exes also attended.

Jason Sudeikis, 47, has made his mark on the acting industry over the years with impressive roles in Ted Lasso, 30 Rock, It’s Always Sunny In Philadelphia, and more, but he’s also led an active dating life, which includes one marriage. The talented star previously got hitched to Kay Cannon, and after their divorce, had a high-profile romance with Olivia Wilde. He also dated a few others along the way.

Find out more about Jason’s first and only marriage as well as his past known relationships below.

Kay Cannon

Jason met writer and director Kay in the late 1990s. He was doing improv in Chicago, IL at the time and the two hit it off. They ended up dating for several years and one year after he was hired as a writer for Saturday Night Live, they tied the knot in 2004. Jason had to spend time away from Kay in New York City, NY, where the SNL studios were located, and he later opened up about how he eventually approached Lorne Michaels for 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 choose one … ‘ ” Jason said in an interview with GQ in 2021.

He became a cast member and a few years later, his marriage with Kay stopped working. He also talked about how that situation was and how it affected his work, in the open and honest GQ interview. “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 explained.

Jason and Kay went their separate ways in 2008 but their divorce wasn’t finalized until 2010. They still remain friendly and after Jason’s Golden Globe Award win in 2021, Kay even shared a message of support on Twitter. “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,” she wrote.

January Jones

After Jason’s marriage with Kay didn’t work out, he went on to reportedly date actress January Jones. They were first seen together at an ESPY afterparty in July 2010 and were later seen on set of a movie Jason was filming at the time. They were also photographed grabbing lunch together in Los Angeles, CA around the same time. After sparking romance rumors, Jason confirmed their relationship, in an interview on Lopez Tonight, per Huffington Post.

Despite having a “great” time together, Jason and January called it quits in Jan. 2011. After reportedly being “on and off” for a few months, sources said that distance was the reason things didn’t work out.

Olivia Wilde

After his time with January, Jason went on to meet Olivia at a SNL afterparty in 2011. Olivia admitted she was “there as a date of someone else,” during an interview on The Howard Stern Show. “I was looking for this person, and [Jason] 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!’,” she explained. He ended up walking away without getting her number, but they later kept bumping into each other at various events over the course of six months and Olivia eventually asked her best guy friend to give her number to Jason. It led to their first date, which was at a restaurant in New York City, in the fall of 2011, and it grew from there.

In Oct. 2013, Jason and Olivia announced that they were expecting their first child and they got engaged after he proposed to her just a few months later. Their son, Otis Alexander, was born in Apr. 2014 and he was followed by their daughter, Daisy Josephine in Oct. 2016. Despite being open about their love for each other throughout the years, the lovebirds ended their engagement and went their separate ways in Nov. 2020, just short of their 10-year anniversary as a couple.

After their split, Jason and Olivia went through a custody battle for their two children. Olivia was served with legal documents concerning the matter during an appearance at CinemaCon in Las Vegas, NV in 2022. Although they continue to work out arrangements, Olivia said that their children are and always will be their number one priority and they both just want what’s best for them.

Keeley Hazell

Seven months after Jason’s split from Olivia, he was seen packing on PDA with his Ted Lasso co-star Keeley Hazell, whom he first met while filming Horrible Bosses 2 seven years prior. They were also seen kissing during a trip to Cabo San Lucas, Mexico in Nov. 2021, and were first linked in Feb. 2021, according to US Weekly. A source told the outlet that they started out as “just friends” but it turned romantic shortly after Jason was single again. Sadly, the couple didn’t last, and called it quits in May 2022. After their split, they made headlines when they both attended the premiere of the final season of Ted Lasso in Mar. 2023, but they did not pose together.