A Look At Olivia Wilde And Jason Sudeikis’ Relationship Timeline: From Love To Separation

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As I delve deeper into the intriguing lives of Jason Sudeikis and Olivia Wilde, I can’t help but be captivated by their rollercoaster journey. Their love story, marked by parenthood, adoption, and heartbreak, is a testament to the complexities of human relationships.

Fate or destiny is believed to play a significant role in whom we end up marrying. For some individuals, their love story becomes an eternal one, while for others, such as Olivia Wilde and Jason Sudeikis, their love journey may lead them to part ways eventually.

Back in 2011, following our personal life upheavals, I stumbled upon a spark at a hushed-down Hollywood soiree post a late-night Saturday Night Live episode. The charismatic Olivia Wilde and I, a former SNL cast member, crossed paths, both of us treading the path of new beginnings after our respective divorces. Olivia, the visionary director of Booksmart, had been previously married to Tao Ruspoli from 2003 to 2011, while I shared my days with Kay Cannon from 2004 to 2010. Instantly, there was a connection that kindled between us, like two stars aligning in the night sky.

Back in October 2013, I got the thrilling news that my beloved couple was expecting their first child. Fast forward to 2016, and there was another precious little one on the way! Seven years of blissful engagement and creating a beautiful family together… but then, in November 2020, it broke my heart when Us Weekly reported that after all this time, the romance between them had sadly ended.

Regardless of being apart, they both actively supported each other’s endeavors and continue to be committed parents to their shared kids, functioning as cooperative parenting partners.

Examine the chronology of Olivia Wilde and Jason Sudeikis’ romantic journey, from their meeting that sparked love, to their decision to part ways.

         

1. May 2011: Jason Sudeikis and Olivia Wilde meet at a Saturday Night Live finale party

Sudeikis and Wilde crossed paths for the first time on the SNL set. As Wilde shared with Allure later, it was Sudeikis’ dancing skills that caught her attention. “I met Jason and found him incredibly charming,” she said. “He’s a fantastic dancer, and I can’t resist good dancers. But he didn’t even get my phone number,” she added to the publication.

Although he had her phone number, Sudeikis didn’t reach out to her initially. However, over the course of six months, we continued to cross paths. She recalled this incident in an interview with Allure, explaining that one evening, her best male friend approached Sudeikis and handed him her phone number, saying, “This is Olivia’s number. Feel free to use it.” This seemingly casual encounter marked the start of their relationship.

After they started conversing, they ventured out for their initial date. “Initially, I assumed he wouldn’t find me appealing; I didn’t think I stood a chance,” she admitted. “He was just so charismatic, so witty—I’ve always admired him and appreciated his quickness and intelligence,” she continued. “He’s an exceptionally talented actor with a mind that moves as swiftly as lightning,” she concluded.

 

2. December 2011: Jason Sudeikis and Olivia Wilde are spotted together at a sporting event

In December 2011, the pair were both sporting identical University of Kansas Jayhawks hats at a team baseball game. Even though they didn’t openly acknowledge it, it was evident that there was a strong, simmering connection or attraction between them.

A year after their first interview together, it appeared that their relationship had deepened significantly. In an October 2012 chat with USA TODAY, Olivia Wilde shared that she and Jason Sudeikis were residing in New York City with their pet dog Paco. Later in the same month, they were spotted locking lips while traveling in Rome. While Wilde was busy filming her new project, “The Third Person,” this affectionate display hinted at the growing seriousness of their bond.

3. January 2013: Jason Sudeikis proposes to Olivia Wilde

In the 1920s Parisian style, Wilde received an engagement ring featuring a circle of emeralds surrounding a central diamond. As shared with Marie Claire, Sudeikis had been carrying this precious token for a whole month prior. A source then told PEOPLE that they were extremely thrilled and very, very joyful at the time.

Back in April 2013, the actress expressed her desire to have three children with Jason Sudeikis, stating that she wasn’t in a hurry to begin their family journey.

She couldn’t help but imagine Sudeikis as a father. He was so good with kids that, for the first time, she found herself thinking, “He’s the person I want to raise a child with.”

                 

4. October 2013 – April 2014: Birth of first and second child 

Back in October 2013, it was announced by Jason Sudeikis and Olivia Wilde that they were going to become parents for the first time. Their representatives revealed this news first to PEOPLE magazine, mentioning that the couple was overjoyed and eagerly anticipating adding a new family member.

Approximately six months later, on April 20th, 2014, their son, Otis Alexander Sudeikis, made his arrival. Wilde announced his birth on Twitter several days after it occurred, posting, “Ladies and gentlemen, Otis Alexander Sudeikis has checked out of the maternity ward! (I’m the maternity ward),” along with a heartwarming black-and-white image of her and the newborn.

5. July 2017: Jason Sudeikis and Olivia Wilde adopt a dog together

Following the confirmation of their first pregnancy in October 2013, and then welcoming another child in 2014, Jason Sudeikis and Olivia Wilde were firmly dedicated to one another. They made multiple appearances on various television programs and prioritized nurturing their expanding family.

Back in July 2017, I proudly unveiled to the world the latest addition to ours, a rescued canine we’ve affectionately named Elvis Sudeikis-Wilde. I took to Instagram to present this charming fellow, who was once called Maxamillion, with the caption, “Allow me to introduce you all to the charmer formerly known as Maxamillion.” It became clear then that he was the long-lost member our family had been yearning for.

         

6. November 2020: PEOPLE reports that Jason Sudeikis and Olivia Wilde called off their engagement

Fate seemed to have it planned, as People magazine reported in November 2020 that Jason Sudeikis and Olivia Wilde had called off their engagement of over seven years. A source confirmed that the separation was peaceful, and the former couple have since established an effective co-parenting arrangement.

1. The family values its children as the priority and core of their bond, according to the source. Yet, surprisingly, the former partners appeared amicable even after their separation, as they were seen exchanging a warm embrace in Los Angeles on November 17, 2020.

7. January 2021 to February 2021: Both Jason Sudeikis and Olivia Wilde were seen moving on with new partners 

In the start of 2021, Olivia Wilde was spotted walking hand-in-hand with Harry Styles at a wedding. The duo, who initially crossed paths during the production of Wilde’s movie “Don’t Worry Darling”, were rumored to be in the initial phases of their relationship. A source shared with PEOPLE that they had been dating for several weeks, highlighting their affectionate behavior towards each other and visible happiness around their companions.

During the same month, an insider shared with PEOPLE that Jason Sudeikis was deeply saddened by his breakup with Wilde. This source added that they held strong feelings for each other, and Sudeikis harbored hopes of finding a way to mend their bond.

By February 2021, it was reported that Sudeikis was casually seeing British model Keeley Hazell. A source told PEOPLE that the two, who had previously collaborated on Horrible Bosses 2, were spending time together, but Sudeikis wasn’t seeking anything serious at the moment.

       

8. Legal battle between Jason Sudeikis and Olivia Wilde

In the month of April 2022, while performing on stage at CinemaCon, Olivia Wilde received court documents from Jason Sudeikis concerning their children’s custody. This unexpected event generated a lot of buzz and an awkward situation.

Later on, Wilde accused Sudeikis of intentionally attempting to humiliate her and cause disruption during her presentation. However, Sudeikis denied any prior knowledge about the method of delivery and had asked for a less conspicuous service instead.

By August 2022, I aimed to dismiss Sudeikis’ custody petition that was initially filed in New York. However, due to lack of jurisdiction, the case was withdrawn, keeping it in California. In our ongoing custody battle, a source shared that while we no longer interact directly, our primary focus remains ensuring the best for our children. Both of us are committed to maintaining their wellbeing amidst this situation.

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2024-08-26 17:40