From January Jones to Olivia Wilde

Jason Sudeikis is not looking for anything serious after his split from Olivia Wilde.

But before the actor made headlines for his relationship with Wilde, he married writer and director Kay Cannon. While their marriage only lasted a few years, during that time Sudeikis skyrocketed to fame thanks to his role in the film. Saturday night life. By the time she finished her eight-year run on the show in 2013, she had split from Cannon and was newly engaged to Wilde.

The couple had two children together in nine years, but announced in 2020 that they were separating. Since then, their separation and subsequent detention has been in the media. Although Sudeikis kept the details as private as possible, he did share how the end of the couple’s relationship affected him.

“In a year, I’ll understand why. And an even better one from the second, and an even bigger one from every fifth. You know, the book of my life becomes a chapter. From paragraph to line, a word and a scribble,” Sudeikis said. GQ.

Since then, Sudeikis has been linked to his belt Ted Lasso co-star Keeley Hazell, though they broke up in 2022.

Here’s a look at Jason Sudeikis’ dating history.

Kay Cannon

In the late 1990s, Sudeikis met writer and director Kay Cannon while improvising in Chicago. After several years of dating, they tied the knot in 2004.

During their relationship, Sudeikis accepted a job as a writer Saturday night life and moved to New York. He told me later GQ he became “unhappy” living away from his wife and being a writer, so he approached creator Lorne Michaels as a crew member.

“He had the best line. I’m like, ‘I had to give up two things to take this writing job: acting and living with my wife.’ And on a dime he just says, ‘Well, if you had to choose one …” Sudeikis said in an interview GQ in 2011.

A few years after becoming a cast member of the hit show, Sudeikis and Cannon split in 2008. Their divorce was finalized in 2010.

More than a decade later, Cannon proved the former couple are still on good terms when he congratulated his ex on the Golden Globes. “A lifetime ago I watched the #goldenglobes with @jasonsudeikis when he was tall and in a hoodie. Congrats on your win, dumbass! And congrats to the cast and crew of @TedLasso. So good, funny. & heartfelt show. #believe,” Cannon he wrote on Twitter in 2021.

January Jones

In July 2010, Sudeikis sparked dating rumors Crazy men January Jones is an actress. The pair were reportedly first spotted dating at an ESPY afterparty, and were later spotted on the set of a movie Sudeikis was filming at the time. They were then photographed together while having lunch in Los Angeles.

When Sudeikis was later asked about the relationship during an appearance Lopez tonight, according to HuffPost. He confirmed that they were dating – although he hesitated to answer if he had seen her “naked and all”. Despite initially saying she “didn’t want to get into it,” she jokingly added, “I want to get into it! Me too, and I have!”

Jones later responded to her comments, telling PEOPLE, “He’s never seen me naked and he never will.” Although he later added: “I think he handled that issue very well. He made a joke out of it. What should he have said?”

Only days later, Sudeikis said Vanity Fair that Jones was “great” and “very happy about everything” – but unfortunately their happiness didn’t last long. Sources told PEOPLE that the distance strained the couple’s relationship, and they finally called it quits in January 2011 after “being on and off for a few months.”

Olivia Wilde

Sudeikis first met Olivia Wilde in Saturday night life Afterparty in May 2011. “I was there as someone else’s date,” he later recalled The Howard Stern Lecture. “I was looking for this person and [Sudeikis] he said, “Whatever you’re looking for, you don’t need it.” But he claims that “it was true, not a line!” Sudeikis didn’t say anything else before he left — and he left without knowing Wilde’s number.

Over the next six months, the duo saw each other frequently at events but still failed to connect. Wilde eventually took matters into her own hands and recruited her best friend to give Sudeikis her number.

The couple had their first date that same fall at a New York restaurant. At the end of the date, Wilde said she was “madly in love”. They started dating in November 2011.

Sudeikis proposed to Wilde after the holidays in 2012, and a source told PEOPLE at the time, “They are so excited … and very, very happy.”

In October 2012, they announced that they were pregnant with their first child, and six months later their son, Otis Alexander, was born.

“In a lot of ways, a child is more of a commitment. We’re totally committed and we’re really happy as a family,” Wilde said. Brightness when asked about wedding plans. “And a ‘normal family’ no longer has a definition. Today’s children grow up with 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’s going to be really fun.”

The engaged couple welcomed their second child, daughter Daisy Josephine, in April 2016. The following year, they found the “missing member” of their brood when they adopted their dog, Elvis.

In November 2020, news broke that Sudeikis and Wilde had ended their engagement. The actress later revealed that the couple had “broken up at the beginning of the year [COVID-19] pandemic.” Sources told PEOPLE that the split was “amicable” and that the former couple kept their children “primary.” Sudeikis and Wilde were on good terms when they were spotted cuddling just days after the split was announced.

However, their relationship took a turn when Wilde and Harry Styles’ relationship broke in early 2021. However, a source revealed to PEOPLE that Sudeikis is still “absolutely devastated” over the breakup and hoped the former couple had a way to patch things up. A few months later, Sudeikis spoke publicly about the breakup for the first time, sharing that he was trying to learn from the experience.

“It’s an experience from which you either learn or make excuses. You take responsibility for it, you hold yourself accountable for what you do, and then you try to learn something obvious from it,” he said in an interview. GQ.

In April 2022, details of the former couple’s custody battle were made public when Wilde was served legal documents at CinemaCon in Las Vegas. While a source told PEOPLE that Sudeikis had “no prior knowledge” of how the documents would be served, Wilde later accused Sudeikis of being intentional in court documents she filed to deny custody of their two children. your request regarding your right.

“Jason’s actions were clearly intended to threaten and catch me off guard. He could have served me discreetly, but instead chose to serve me in the most aggressive manner possible,” Wilde claimed in his court filing.

In his own submission, Sudeikis reiterated that he had not intended for Wilde to receive the papers on stage, but added that “I didn’t want the service to be at Olivia’s current partner’s home because Otis and Daisy might be there.” According to court documents later obtained by PEOPLE, a New York judge granted Wilde’s motion to dismiss Sudeikis’ request because the state lacks jurisdiction over child custody requests.

Wilde later spoke about the situation, saying that during CinemaCon, “so many different people and trying to “sabotage the studio’s work” was “really mean”. He noted that the incident “wasn’t a complete surprise” to him and admitted that he “had a reason.” [she] has left this relationship.”

Amid the legal drama, a source told PEOPLE that Wilde and Sudeikis are no longer on speaking terms and need help communicating about their custody schedule. But despite their differences, Wilde recently said that she and Sudeikis have the same intentions for their children.

“They’re my priority. That’s it. As long as they’re happy and healthy, my ex and I agree on that. They mean everything to us. There’s so many families that mix. But you know, it’s tricky because we don’t do it in private,” Wilde shared. .

Keeley Hazell

In early 2021, Sudeikis was spotted spending time with his Ted Lasso co-star Keeley Hazell. Sources told PEOPLE that Sudeikis and Hazell “knew each other from years ago” after first meeting on set. Horrible Bosses 2where he played Chris Pine’s assistant.

Shortly after the pair were first spotted at Hazell’s London home, she was wearing the same rainbow tie hoodie that Sudeikis wore during her virtual appearance at the Golden Globes that year. She even posted an Instagram story of herself in front of a fireplace that was almost identical to the one behind Sudeikis during the awards show.

While the couple began dating rumors, sources say Sudeikis wasn’t looking for anything serious at the time. That June, things seemed to heat up for the pair as they were spotted hooking up during a trip to New York, seemingly cementing their romance. But they kept things quiet for the rest of the summer, prompting sources to say they’re “just friends” again. The pair were not photographed together again until September, when they were seen on an outing in Los Angeles.

However, they reportedly divorced in 2022.