Ted Lasso star Jason Sudeikis recently opened up about his past relationship with Olivia Wilde, admitting that communication problems contributed to their separation. During an October 2026 appearance on the Talk Easy with Sam Fragoso podcast, the actor reflected on their nine-year relationship and acknowledged that he could have expressed his feelings more clearly.
The discussion renewed interest in Sudeikis’ romantic history, particularly his former marriage to screenwriter Kay Cannon and his long engagement to Wilde. Although many people associate Wilde with the actor’s family life, the two were never married. Sudeikis was previously married to Cannon, and he publicly confirmed in June 2026 that he was single.
Who Is Jason Sudeikis’ Wife?
Jason Sudeikis does not have a publicly confirmed wife. His only known marriage was to Kay Cannon, an American screenwriter, producer and director recognized for her work on 30 Rock, Pitch Perfect and Blockers.
Cannon and Sudeikis married in 2004, before either became widely recognized for their achievements in television and film.
Their relationship developed during their early comedy careers, when both were involved in improvisational theater. However, their marriage encountered difficulties as their professional responsibilities increased.
The couple separated in 2008 and finalized their divorce in February 2010. They did not have children together.
Following their divorce, Cannon continued building her career as a writer and filmmaker, while Sudeikis became a familiar face on Saturday Night Live and later established himself as a leading comedy actor.
Jason Sudeikis and Olivia Wilde’s Relationship
Jason Sudeikis began dating actress and filmmaker Olivia Wilde in 2011 after meeting her at a Saturday Night Live finale party.
Their relationship quickly became serious, and they were frequently photographed together at Hollywood events. Sudeikis proposed in January 2013, presenting Wilde with a vintage-style engagement ring.
Although they remained engaged for several years, the couple never officially married.
During their relationship, Wilde continued working as an actress and director, while Sudeikis appeared in films including We’re the Millers and Horrible Bosses 2.
The couple also supported each other’s professional projects. Wilde directed Sudeikis in her 2019 film Booksmart, while he publicly acknowledged her contribution to the development of Ted Lasso.
Their relationship ended in 2020 after approximately nine years together.
Why Did Jason Sudeikis and Olivia Wilde Separate?
Sudeikis and Wilde’s separation became public in November 2020, ending their seven-year engagement.
Their breakup attracted considerable media attention, particularly after Wilde began dating singer Harry Styles.
In October 2026, Sudeikis discussed the relationship during an interview on the Talk Easy podcast. He acknowledged that communication had been one of the difficulties in their relationship.
The actor explained that he could have been more open about his emotions instead of expecting his partner to understand feelings he had not expressed.
Despite their separation, Sudeikis spoke positively about Wilde’s professional achievements and described himself as fortunate to have gained perspective from their experiences.
The former couple have continued sharing parenting responsibilities for their two children.
Jason Sudeikis and Olivia Wilde Have Two Children
Jason Sudeikis and Olivia Wilde share two children, a son named Otis Alexander Sudeikis and a daughter named Daisy Josephine Sudeikis.
Otis was born on April 20, 2014, while Daisy arrived in October 2016.
Following their separation, the former couple experienced disagreements over custody arrangements. They eventually reached a joint custody agreement in 2023.
Both parents have continued prioritizing their children’s well-being while maintaining separate professional and personal lives.
During a June 2026 appearance on the Friends Keep Secrets podcast, Sudeikis explained that fatherhood had changed his approach to relationships.
He emphasized that his children would remain his priority in any future romantic relationship. He also revealed that he would consider having more children if he fell in love again.
Is Jason Sudeikis Dating Anyone Now?
Jason Sudeikis has not publicly confirmed a new wife or serious relationship.
Following his separation from Wilde, he was romantically linked to British actress and model Keeley Hazell, who appeared in Ted Lasso. Their relationship reportedly ended in 2022.
In June 2026, Sudeikis confirmed that he was single and discussed the challenges of dating while raising children.
The actor explained that he was not particularly interested in dating several people simultaneously, describing the experience as overwhelming.
For now, Sudeikis remains focused on his children and entertainment career. Although his relationships with Kay Cannon and Olivia Wilde have attracted public attention, he has kept much of his personal life private since their separations.