What Went Wrong With Jason Sudeikis And Olivia Wildes Relationship?

Olivia Wilde and Jason Sudeikis were everyone’s favorite celebrity couple in the 2010s. They were together for nearly nine years, including the seven years they were engaged. The couple never missed a moment to gush about the other, demonstrating their appreciation for each other and highlighting the other’s work in the industry. Together they have two children, Otis and Daisy.

Wilde and Sudeikis’s split in 2020 came as a complete shock. Even though they were never officially married, fans thought the two of them would be together forever. Fans were even more shocked when they witnessed Wilde be served custody papers from Sudeikis on stage at CinemaCon. Something clearly went very wrong in their relationship, so let’s get into everything that happened between Jason Sudeikis and Olivia Wilde’s relationship.

Related: How Close Is Jason Sudeikis To His Ex Wife, Olivia Wilde?

8 When Did Jason Sudeikis And Olivia Wilde Meet?

Jason Sudeikis and Olivia Wilde met in May of 2011. Specifically, they met at an after party for an episode of Saturday Night Live. Wilde has since spoken out about their first meeting, and it seemed like attraction at first sight. Wilde has always had an appreciation for good dancing, and Sudeikis certainly showed off his moves at the party.

Unfortunately for Wilde, after she made the first move, Sudeikis did not ask for her number. She had to wait until a friend of hers gave Sudeikis her number and told the actor to use it. Even then, Sudeikis waited a long time to finally text Wilde.

7 Jason Sudeikis Waited Four Dates To Kiss Olivia Wilde

Apparently, Jason Sudeikis is a man who likes to take things slow. After waiting months to finally text Olivia Wilde, they finally went on their first date. Sudeikis was a gentlemen and did not advance for a kiss that night, which was fine with Wilde until she had to wait four dates for that first kiss.

Wilde spoke to Howard Stern about when she and Sudeikis shared their first kiss. “He literally didn’t kiss me until the fourth date,” she shared. “He finally kissed me. And I was like, completely head over heels.”

6 When Did Jason Sudeikis And Olivia Wilde Start To Live Together?

In the early days of their relationship, Jason Sudeikis and Olivia Wilde seemed to be in perfect bliss. They both have crazy work schedules with Sudeikis’s acting and Wilde’s directing, but they clearly made time for each other.

Wilde spoke to US Today about how they chose to move in together in October 2012. “I’ve been decorating our new apartment,” she revealed, and she seemed thrilled to be taking the next step with Sudeikis. “I’m so domestic.”

Related: Fans React To Jason Sudeikis Finally Addressing His Breakup With Olivia Wilde

5 Jason Sudeikis Proposed To Olivia Wilde

Jason Sudeikis and Olivia Wilde certainly intended to spend the rest of their lives together. After carrying a ring around for over a month, Sudeikis finally popped the big question to Wilde in January 2013. Fans were overjoyed for the couple, and the two seemed as happy as could be.

He proposed with a 1920s Parisian engagement ring. The ring had a circle of emeralds around a center diamond. They did not make any immediate plans for a wedding, and the waiting ended up dragging out for 7 whole years of engagement.

4 How Many Kids Do Jason Sudeikis And Olivia Wilde Have?

Wilde once shared that she wanted to have three children with Sudeikis. They came fairly close to reaching that goal, as the couple shares two children. Their son Otis was born in April 2014, and their daughter Daisy came into the world in October 2016.

The family of four lived together while Sudeikis and Wilde were still together. There has been much debate between the two over where the children will live now that they have split up. Wilde won the first custody battle, determining that their children will remain in Los Angeles with her even though Sudeikis spends his time in New York City.

3 Were Jason Sudeikis And Olivia Wilde Ever Married?

Considering they were together for so long, fans are always surprised to learn that Jason Sudeikis and Olivia Wilde never officially tied the knot. They were engaged from the proposal in 2013 to their split in 2020. Seven years is certainly a very long time to be engaged without hearing any wedding bells!

However, their long engagement did not bother them. Wilde spoke to People to discuss their wedding plans, saying “We’re engaged, but no specific plans yet.” The director also added that “there’s no definition of the ‘normal family’ anymore.”

Related: Jason Sudeikis Mocked For Being ‘Heartbroken’ Over Oliva Wilde And Harry Styles

2 When Did Jason Sudeikis And Olivia Wilde Break Up?

The news came in November 2020 that Jason Sudeikis and Olivia Wilde had called it quits. The split was heartbreaking to many, including Sudeikis and Wilde. Fans wondered how the two would handle co-parenting their children, especially considering their work schedules.

A source revealed to People that “it’s been amicable and they’ve transitioned into a great co-parenting routine.” The source also made a point to highlight how “the children are the priority and the heart of the family’s relationship.”

If the news of their split did not shock fans, Sudeikis’s actions at CinemaCon certainly did. Olivia Wilde was at CinemaCon to give a presentation on her upcoming film Don’t Worry Darling, which will star Florence Pugh and Harry Styles. In the middle of her presentation, Wilde was served legal custody papers. She was forced to acknowledge the paper work and then carry on in front of the live audience.

Fans applauded her ability to move forward, but her composure did not eliminate the embarrassment she felt. Though Sudeikis has claimed he had no idea when the papers would be served, that is unlikely considering the circumstances. Wilde claims Sudeikis meant to embarrass her.

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