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

usmagazine.com:

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.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