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Jason Sudeikis’ Dating History: Olivia Wilde, January Jones and More

Believe … in love. Jason Sudeikis‘ romantic life has had its fair share of ups and downs, but he’s never stopped seeking a fulfilling relationship.

The Ted Lasso star was first married to Pitch Perfect screenwriter Kay Cannon, whom he met in Chicago in the early 2000s while doing improv at the Second City. The couple married in 2004 after Sudeikis moved to New York City for a writing job for Saturday Night Live.

During an August 2021 interview with GQ, the comedian shared that he was “unhappy” before being bumped up to a featured player after a conversation with showrunner Lorne Michaels.

“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 —,’” he shared, adding that his separation from Cannon made him “feel like a crazy person” and ultimately put a strain on their relationship.

Jason Sudeikis Dating History Olivia Wilde January Jones More

The pair separated in 2008 and divorced in February 2010. They still, however, remain on good terms, as Cannon dedicated a sweet tweet to her ex following his March 2021 Golden Globes win for lead actor in a comedy or musical series for Ted Lasso.

“A lifetime ago, I spent several years watching the #goldenglobes w/ @jasonsudeikis while he was high & wearing a hoodie,” the Blockers director quipped, pointing to Sudeikis’ notable choice of dress that night. “Congrats on your win, ya wanker! And congrats to the cast & crew of @TedLasso. Such a great, funny & heartfelt show. #believe.”

After his divorce from Cannon, the Horrible Bosses actor went on to date Mad Men star January Jones in 2010 after they met during her hosting gig on SNL in November 2009.

Sudeikis described the headline-making romance as his “first sort of public relationship” to GQ in August 2021, saying it ended up being a “trial by fire” situation as he became a more prominent figure in the industry.

The couple went their separate ways in January 2011, ultimately blaming the separation on being long-distance. (Jones was shooting Mad Men in L.A. while Sudeikis was living in New York for SNL).

“The long-distance kind of petered us out,” the actress told Allure in a May 2011 interview. “When you date someone else who’s in the industry, someone has to make the sacrifices. And if no one’s willing to, then you just have to be friends.”

Sudeikis and Olivia Wilde began dating in November 2011 after meeting at an SNL wrap party in May following the show’s season 36 finale.

After two years of dating, the Virginia native popped the question to Wilde. Though they never tied the knot, the Don’t Worry Darling director welcomed their son, Otis, in April 2014. They went on to have a daughter, Daisy, in October 2016.

In November 2020, Us Weekly confirmed that the couple had called it quits. Two months later in January 2021, Wilde sparked romance rumors with musician Harry Styles, but a source told Us that Sudeikis was “desperate” to win his ex back.

While the couple didn’t reconnect, they initially tried to stay focused on having a healthy coparenting relationship and have often supported each others’ professional successes.

“Olivia and Jason are better off as friends. They’re doing their best at giving their kids a normal life,” a source told Us in July 2021. “The kids bring them back together since they are and always will be their number one priority.”

The exes continue to face challenges, however, amid their ongoing custody battle. While they’ve both remained tight-lipped about the circumstances of their breakup, in April 2022, the duo made headlines when Wilde was publicly served with legal papers during an appearance at CinemaCon.

“Papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” a source exclusively told Us at the time, noting that the Last Man on Earth star didn’t know when the documents would be delivered. “He would never condone her being served in such an inappropriate manner.”

Wilde subsequently fired back, saying that her ex’s actions were “clearly intended” to “threaten” her and catch her “off guard.”

“He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible,” the actress said in court documents obtained by Daily Mail in August 2022. “The fact that Jason would embarrass me professionally and put our personal conflict on public display in this manner is extremely contrary to our children’s best interests.”

Following his separation from Wilde, Sudeikis was linked to British model Keeley Hazell in February 2021 after they met while filming Horrible Bosses 2. A source told Us at the time, however, that the actor wasn’t “ready for any type of serious relationship.”

Four months later, the duo were seen getting cozy in New York City, hugging and walking hand in hand. After their June outing, a source confirmed the two were dating, and they were again photographed kissing in November 2021 while on vacation in Cabo San Lucas, Mexico.

Their relationship ended in May 2022 about a year after they began dating.

Scroll down to revisit the Eastbound & Down actor’s various romances: