The Stunning Women Jason Sudeikis Has Dated Over The Years

Jason Sudeikis has been in the spotlight for decades, and in that time, he's had a number of high-profile relationships. Naturally, all of his IRL leading ladies have been gorg, too. 

Fans of Sudeikis may know that when he got his first big break on "Saturday Night Live" (as a writer, rather than a star), he was already married to fellow writer Kay Cannon. Yep, the same Cannon who would go on to write for "30 Rock" and later the "Pitch Perfect" films. In addition to her work behind the scenes, Cannon has also worked as an actor from time to time, appearing on "New Girl" as Sadie's wife Melissa — and like we said, she's stunning. In fact, if you didn't know who you were looking at, she could easily be mistaken for Aubrey Plaza.  

Of course, Cannon and Sudeikis' marriage ultimately didn't work out, and the "Ted Lasso" star has cited his "SNL" career as one of the reasons why, telling GQ he'd struggled with living away from his wife, who was based in Las Vegas. Speaking to Reuters while promoting his 2011 film "Hall Pass," Sudeikis shared that they'd separated in 2008. He then revealed, "The divorce was finalized during the shooting of this movie." It does seem as though the split was a friendly one, and some may even recall Cannon taking to X to congratulate her ex on winning a Golden Globe for "Ted Lasso" in 2021. However, she subsequently deleted her account, so the post is no longer visible. Sudeikis' ex-wife moved on with fellow writer Eben Russell, and the couple shares a daughter. 

Millennials will no doubt remember that back in 2010, Jason Sudeikis and January Jones' relationship made a ton of headlines. Rumors of a romance between the "SNL" star and the "Mad Men" bombshell and former model were first reported on in July of that year, and in September, Sudeikis acknowledged that they were together. "We're dating, she's great. I'm very happy with everything," he told Vanity Fair. 

Unfortunately, because of how high-profile both Sudeikis and Jones were at the time, their relationship got a ton of attention. Looking back on that time with GQ in 2021, he compared it to a "trial by fire." Ultimately, even though he and the "Mad Men" star continued to spark headlines throughout 2010, by early 2011, they'd already parted ways. Speaking to People at the time, a source confirming the split explained, "They've been on and off for a few months and then the long distance kind of ended it." The insider seemed to be hopeful for the future, though, adding, "They could get back together. It was just hard to stay together with the distance."

Well, never say never (getting back together ... yes, we sang that), and perhaps at some point Jones and Sudeikis will revisit their romance. However, for more than 10 years since their split, that hasn't happened.

Next up we have what's arguably been Jason Sudeikis' most high-profile relationship to date, actor and former Maxim Hot 100 2009 winner, Olivia Wilde. Their romance timeline began in late 2011, and in early 2013, they got engaged. However, as fans of the couple will know, they never officially tied the knot. 

Despite not getting married, Sudeikis and Wilde would welcome their first child, son Otis, in 2014. Speaking to Glamour in August of that year, the "Tron" star shared, "In many ways, a child is more of a commitment. We are fully committed and really happy as a family" (via People). They would become parents a second time in 2016, this time to daughter Daisy. 

Sadly, Wilde and Sudeikis split in 2020, though at the time, things seemed to be fairly friendly. A source who spoke with People shared of their relationship post-breakup, "It's been amicable and they've transitioned into a great co-parenting routine." And, for a while, things were very friendly. So friendly, in fact, that Wilde moved in with Sudeikis while he filmed "Ted Lasso" during the pandemic, and Sudeikis thanked his ex in his Critics' Choice Award acceptance speech in March 2021. However, things infamously took a turn when the actors began battling over custody, and in one particularly dramatic moment, Wilde was served with legal papers at CinemaCon in 2022. While on stage. Sudeikis denied planning it, and in a 2026 appearance on "Call Her Daddy," Wilde shared, "I need to believe that in order to continue." She also shared that they were great co-parents and actually did a better job at parenting than they had when they were still together. Small wins, we guess!

In the wake of his split from Olivia Wilde, Jason Sudeikis was linked with yet another stunner. This time, Sudeikis' love interest was British former model (and his "Ted Lasso" co-star), Keeley Hazell. 

Neither Sudeikis nor Hazell ever discussed their relationship themselves, but insiders regularly spoke about it with the press — though with the co-stars spotted hugging and kissing in Cabo over Thanksgiving 2021, they didn't really need to. Sources who knew the pair did address it, and clarified that while the actors were definitely dating, there were no expectations on either side. "It's never been a serious thing. They're just enjoying each other's company," one told People. Sudeikis and Hazell reportedly split for good in 2022, supposedly over their clashing schedules. 

The "Horrible Bosses" star would keep his love life quiet in the years that followed, which is understandable given the past drama, as well as the fact that he was a dad. In an appearance on "Friends Keep Secrets," the comedian admitted that dating as a single parent was awkward because his kids would always be his top priority. "They're never number one on the call sheet," he explained of any would-be prospects. Even so, he added that he also had some concerns over that, like the fact that he knew he needed to fill his own cup in order to be a better parent, too. Well, when that day comes, we have no doubts that his next Mrs. (or Mrs.-to-be, anyway) Right will be just as gorgeous as his past leading ladies have been.