If you search for jason sudeikis and wife, you’re going to find a lot of photos of Olivia Wilde. That's the first mistake. Most people assume they were married. They weren't. Not even a little bit.
They were engaged for seven years, which is basically a lifetime in Hollywood, but they never actually walked down the aisle. It's wild how the internet just assigns "wife" status to anyone who stays together long enough to have two kids and a mortgage. Honestly, Jason Sudeikis has only ever had one actual wife: Kay Cannon.
The Kay Cannon Years
Most fans know Kay as the genius writer behind Pitch Perfect or the director of Cinderella. Back in the late '90s, she and Jason were just two kids doing improv in Chicago. They were part of The Second City crew, grinding out sets for laughs and probably eating a lot of cheap pizza.
They got married in 2004.
That was the year Jason started writing for Saturday Night Live.
The transition was brutal.
Jason eventually told GQ that he felt "crazy" during that time. He was living in New York for SNL while Kay was elsewhere, and the distance sucked the life out of the marriage. Imagine being dressed as George Bush on live TV while your personal life is imploding backstage. It’s heavy. They separated in 2008 and finalized the divorce in 2010. The cool thing? They’re still friends. She even tweeted a "congrats, ya wanker" message when he won a Golden Globe for Ted Lasso. That's the kind of ex-wife energy we should all aspire to.
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Jason Sudeikis and Wife: The Olivia Wilde Misconception
Then came Olivia. They met in 2011 at an SNL wrap party. Sudeikis has this story about how he just "didn't use a line" and instead played it cool, which apparently worked. By 2013, they were engaged.
Then came the kids. Otis in 2014. Daisy in 2016.
They were the "it" couple.
Until they weren't.
The split in 2020 was messy. It wasn't just "we grew apart" messy; it was "getting served custody papers while on stage at CinemaCon" messy. If you haven't seen the video, Olivia is literally in the middle of a presentation for her movie Don't Worry Darling when a process server hands her a manila envelope. Jason’s team claimed he didn't know it would happen like that, but the optics were... not great.
The Reality of the 2023 Settlement
By late 2023, the dust finally started to settle. They hammered out a custody agreement that actually seems functional.
- Child Support: Jason pays about $27,500 a month.
- The Schedule: They do a "week-on, week-off" rotation.
- The Vibe: They’ve been spotted at their son’s soccer games looking like they can actually stand to be in the same zip code again.
People love to pick sides. Was he the heartbroken "Ted Lasso" in real life? Was she the director who moved on too fast with Harry Styles? The truth is usually somewhere in the boring middle. Relationships are complicated, especially when you're famous and everyone has an opinion on your "wife" who isn't actually your wife.
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Who is Jason Sudeikis Dating in 2026?
Currently, Jason is technically single, or at least he hasn't put a ring on anyone's finger. He was linked to Keeley Hazell (who, fun fact, inspired the name of the character Keeley Jones in Ted Lasso) for a bit. More recently, there have been rumors about him and actress Elsie Hewitt. They were spotted looking pretty cozy in Los Angeles around late 2024 and early 2025, but Jason is notoriously private about his non-Olivia drama.
He’s spent a lot of time recently focused on the New York Liberty and being a "WNBA dad." You can catch him courtside at Barclays Center way more often than you’ll see him on a red carpet with a new partner.
What You Can Learn from the Sudeikis Saga
The big takeaway here isn't just celebrity gossip. It's about how we project narratives onto people. We wanted him to be Ted Lasso—the guy who forgives everything and bakes biscuits. When the CinemaCon thing happened, it broke the spell for a lot of people.
But look at the Kay Cannon situation. They stayed friends. They supported each other's careers long after the romance died. That’s the real "Ted Lasso" move.
If you're following the jason sudeikis and wife trail, stop looking for a secret marriage. Focus on the co-parenting. It’s less "Hollywood drama" and more "two parents trying to raise kids without making it a headline."
To get the full picture of where Jason stands today, keep an eye on his courtside appearances at Liberty games. That’s usually where he’s at his most authentic—no scripts, no manila envelopes, just a guy who really likes basketball and hanging out with his kids.
Next Steps:
Check out the latest court filings if you're curious about the specifics of the 2023 California custody ruling, or look up Kay Cannon's recent directorial projects to see how she's moved far beyond being just an "ex-wife."