From January Jones to Olivia Wilde, Jason Sudeikis's Romances Over the Years

Jason Sudeikis's love life has been a hot topic in recent years. After splitting from Olivia Wilde in November 2020, the "Ted Lasso" star was caught up in some messy drama with the "Don't Worry Darling" director and her former boyfriend Harry Styles. It involved a custody battle between Sudeikis and Wilde, as well as rumors that Wilde left Sudeikis for the "As It Was" singer.

Despite everything that happened, though, it seems the exes have finally put the past behind them. After Wilde and Styles went their separate ways this past November, Wilde was seen embracing her ex-fiancé in photos obtained by Page Six two months later.

While Sudeikis's relationship with Wilde has made countless headlines, she isn't the only famous woman he's dated. In fact, long before the pair met, the actor was actually married to writer and producer Kay Cannon. The two were together for nine years before splitting in 2008. And most recently, he was romantically linked to his "Ted Lasso" costar Keeley Hazell.

Keep reading for all the details on the actor's public relationships over the years.

Kay Cannon (1999-2008)
Getty | Dimitrios Kambouris

Kay Cannon (1999-2008)

Kay Cannon is known for writing and producing the Pitch Perfect films and the comedy series "30 Rock" and "New Girl." She also directed the films "Blockers" and "Cinderella." According to People, Sudeikis met his soon-to-be wife while doing improv in Chicago during the late 1990s. In a February 2011 interview with Reuters (via Huffington Post), Sudeikis revealed he and Cannon officially got together in 1999. They dated for five years before tying the knot in 2004. However, in 2008, they announced their separation, and their divorce was ultimately finalized in 2010.

Despite his relationship not working out, Sudeikis told Reuters that he still "believes in marriage." "I have to accept the fact I'll never know it all. But I wouldn't be where I am today without that relationship," he said, referencing his marriage to Cannon. "Each experience I go through — marriage, my public life, my personal life — I'm learning as I go."

In 2021, Cannon showed support for her ex-husband by congratulating the actor on his Golden Globe win 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 tweeted.

January Jones (2010-2011)
Getty | Jeff Kravitz

January Jones (2010-2011)

In November 2009, Sudeikis met "Mad Men" star January Jones when she appeared on "Saturday Night Live" as a host. However, their dating rumors didn't begin until July 2010 when People reported the two were seen "making out all night" at an ESPYs afterparty. Around the same time, there were also rumors going around that Jones had been visiting Sudeikis at work while he was filming a movie.

Sudeikis reportedly confirmed their relationship a few weeks later while appearing on "Lopez Tonight" (via Huffington Post). When asked if he had seen Jones "naked and everything," the actor initially responded by saying he "didn't want to get into it," but then joked, "I'm kidding. I do want to get into it! I do, and I have!"

Shortly afterward, Jones responded to Sudeikis's quip in an interview with People at the 2010 Emmys. "He's never seen me naked, nor will he after those comments," she said, before adding, "I think he handled that question very well. He made a joke of it. What was he supposed to say?"

Despite the incident, the pair continued to date until January 2011 when People reported they split. "They've been on and off for a few months and then the long distance kind of ended it," a source told the publication.

Olivia Wilde (2011-2020)
Getty | Kevin Mazur

Olivia Wilde (2011-2020)

Sudeikis's most highly publicized relationship was with actor and director Olivia Wilde. According to People, the pair met at a "Saturday Night Live" afterparty in May 2011. Sudeikis opened up about their encounter while appearing on "The Late Show With Stephen Colbert" in April 2017. "We hit it off that night," he said. Since Wilde was dating someone else at the time, Sudeikis said he "didn't make any moves," but once she was single, he said "it was off to the races" for the couple.

In an October 2013 interview with Allure (via People), Wilde said she thought Sudeikis was "so charming" when they met, but noted that he didn't ask for her phone number right away. After the stars kept running into each other for months, one of Wilde's friends helped the pair finally get together. "[One night], my best guy friend walked up to him and said, 'This is Olivia's number. Use it,'" she said. "That was the beginning."

Sudeikis and Wilde officially began dating in November 2011. Then, in January 2013, People reported the couple had gotten engaged shortly after the holidays. "They are so excited," a source told the publication. "And very, very happy."

A year later, the stars welcomed their first child — a son named Otis Alexander — in April 2014. "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)," Wilde tweeted at the time.

In April 2016, the former couple welcomed a daughter named Daisy Josephine. "There goes the neighborhood. Daisy Josephine Sudeikis. Born, like a boss, on #internationaldayofthegirl," Wilde wrote on Instagram alongside a photo of the newborn.

After welcoming their second child together, Sudeikis and Wilde remained engaged for four more years before People reported in November 2020 the pair had called it quits. "The split happened at the beginning of the year," a source said at the time. "It's been amicable and they've transitioned into a great co-parenting routine. The children are the priority and the heart of the family's relationship."

Just days after the news broke, the stars were photographed hugging in photos obtained by People. While they appeared to be on good terms, things seemingly changed after Wilde moved on with Harry Styles. In January 2021, she and the singer were spotted holding hands at a wedding, sparking rumors they were an item. "They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks," a source told People.

After photos of the pair surfaced, a source also told the publication that Sudeikis was "absolutely heartbroken" over his breakup with Wilde. "There is still a lot of love there, and he would like to have hope that maybe there's a way for them to repair things," the source said. "But what happens next remains to be seen."

In April 2022, things between the exes grew even more complicated when the "Booksmart" director was served legal documents while she was on stage at CinemaCon. According to Vanity Fair, those documents turned out to be custody papers from Sudeikis involving the pair's two children. Following the whole ordeal, a source told People that Sudeikis "had no prior knowledge" of when or where Wilde would receive the papers. "He would never condone her being served in such an inappropriate manner," the source said.

That August, Wilde filed to dismiss the custody petition. "Jason's actions were clearly intended to threaten me and catch me off guard. He could have served me discreetly, but instead, he chose to serve me in the most aggressive manner possible," Wilde said in her court filing, according to the Daily Mail. Amid the drama, People reported the stars weren't speaking but hoped to "figure out the best living situation for everyone."

In January 2023, the exes were spotted hugging in photos obtained by Page Six, just two months after news came out that the "Tron: Legacy" actor had broken up with Styles. So while Sudeikis and Wilde are no longer together, it seems they have made amends and are focusing on coparenting their children.

Keeley Hazell (2021-2022)
Getty | Steve Granitz

Keeley Hazell (2021-2022)

Sudeikis then appeared to move on with British model and fellow actor Keeley Hazell. The pair first met while filming "Horrible Bosses 2" in 2013 and then reunited in 2020 while filming "Ted Lasso." Apparently, their friendship turned romantic after Hazell comforted Sudeikis following his split from Wilde.

"When Jason found out about his wife and Harry, Keeley was one of the people whom he turned towards. During this time he was understandably devastated, but she was brilliant and incredibly supportive," a source told The Sun. "He invited her to join him for a dinner with mates in LA, and their flirty banter quickly set tongues wagging. They have met up since, but obviously, it's all very early days."

While the two were caught up in dating rumors, a source told Us Weekly at the time that they weren't officially together. "They have grown closer for sure, but Jason absolutely isn't ready for any type of serious relationship," the source said.

That June, the duo were photographed walking around New York City together with their arms wrapped around each other. "They've been dating for a little while now," an insider told People. "They're just having fun. It's nothing serious at this point."

They dated for a year before Us Weekly reported in May 2022 that Sudeikis and Hazell had broken up.