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A Look At Olivia Wilde and Jason Sudeikis’ Relationship Timeline: From Love To Separation
Explore the key moments of Olivia Wilde and Jason Sudeikis’ relationship timeline. From their engagement, the birth of their children, to their high profile split and legal battles. Read on.
It's often said that in life, who we marry is ultimately determined by the divine destiny. Some couples find love that lasts forever, while others, like Olivia Wilde and Jason Sudeikis, experience love that eventually leads to separation.
Wilde and Sudeikis had a low-key Hollywood romance that began during a late-night Saturday Night Live afterparty. The two met in 2011 following their respective divorces. Wilde, the Booksmart director, had been married to Italian-American filmmaker Tao Ruspoli from 2003 to 2011, while Saturday Night Live alum Sudeikis was previously married to screenwriter and filmmaker Kay Cannon from 2004 to 2010. They hit it off instantly.
In October 2013, it was announced that Wilde was pregnant with the engaged couple’s first child, followed by a second pregnancy in 2016. However, after seven years of being engaged and building a lovely family together, Us Weekly confirmed in November 2020 that the longtime couple’s romance had come to an end.
Despite their separation, the exes continued to support each other’s respective projects and have remained dedicated co-parents to their children.
Take a look at Olivia Wilde and Jason Sudeikis’ relationship timeline, from falling in love to deciding to separate.
May 2011: Jason Sudeikis and Olivia Wilde meet at a Saturday Night Live finale party
Sudeikis and Wilde first met on the set of SNL. According to Wilde, who later opened up to Allure about their first meeting, it was Sudeikis' moves on the dance floor that helped put him on her radar. "I met Jason, and I thought he was so charming. He's a great dancer and I'm a sucker for great dancers. But he didn't even get my number," she told the outlet.
Then despite having her number, Sudeikis did not text her. "But over the next six months we kept running into each other," she told Allure. "[One night], my best guy friend walked up to him and said, 'This is Olivia's number. Use it.' That was the beginning."
Then they began talking and went out on their first date. "I thought, 'He won't be interested in me; I'm not a contender,' " she said. "He was so cool, so funny—I was such a fan of his and had always fancied his speed and his intelligence. He's a brilliant actor with a brain like lightning," he added.
December 2011: Jason Sudeikis and Olivia Wilde are spotted together at a sporting event
The two sported matching University of Kansas Jayhawks hats while attending the team's baseball game in December 2011. Although the duo did not confirm their romance, it was pretty clear that there was intense chemistry brewing between them.
Then, a year later things seemed to get pretty serious between them as in an October 2012 interview with USA TODAY, Wilde revealed that she was living with Sudeikis and her rescue dog Paco in New York City. Later that month, the couple was seen kissing while abroad in Rome.
January 2013: Jason Sudeikis proposes to Olivia Wilde
Wilde was presented with a 1920s Parisian engagement ring, adorned with a circle of emeralds encircling a central diamond. Wilde revealed to Marie Claire that Sudeikis had been carrying the ring around for a month. "They are incredibly excited," a source told PEOPLE at the time, "and very, very happy."
In April 2013, the actress said that she wished to have three kids with Jason Sudeikis and was in no rush to start a family.
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."
October 2013 - April 2014: Birth of first and second child
In October 2013, Jason Sudeikis and Olivia Wilde confirmed that they were expecting their first child. Their representatives shared the news exclusively with PEOPLE, noting that the couple was "incredibly happy" and "very excited to welcome a new member into their family."
Six months later, on April 20, 2014, their son was born. Wilde declared the arrival of Otis Alexander Sudeikis on Twitter several days after his birth, writing, "Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building! (I'm the building)," accompanied by a sweet black-and-white photo of her with the newborn.
July 2017: Jason Sudeikis and Olivia Wilde adopt a dog together
After confirming their first pregnancy in October 2013, followed by the next one in 2014 Jason Sudeikis and Olivia Wilde were deeply committed to each other, appeared in numerous TV shows, and focused on raising their growing family.
By July 2017, Wilde introduced the world to the newest member of their family, a rescue dog named Elvis Sudeikis-Wilde. She shared an Instagram photo of the pup, previously known as Maxamillion, and captioned it, "Ladies and gentlemen, meet the heartbreaker formerly known as Maxamillion," adding that the dog was the "missing member of our brood."
November 2020: PEOPLE reports that Jason Sudeikis and Olivia Wilde called off their engagement
As fate had it in store, in November 2020, PEOPLE noted that Jason Sudeikis and Olivia Wilde had ended their engagement of more than seven years. According to a source, the split was amicable, and the couple had successfully changed into a strong co-parenting routine.
"The children are the preference and the heart of the family's relationship," the source said. However, the exes seemed to be on friendly terms despite their split when they were spotted sharing a hug in L.A. on November 17, 2020.
January 2021 to February 2021: Both Jason Sudeikis and Olivia Wilde were seen moving on with new partners
In early 2021, Olivia Wilde was noticed holding hands with Harry Styles at a wedding. The pair, who had met on the set of Wilde's film Don't Worry Darling, were reported to be in the early stages of their romance. A source told PEOPLE that they had been dating for a few weeks, noting that they were affectionate around their friends and appeared very happy.
Meanwhile, that same month, a source revealed to PEOPLE that Jason Sudeikis was still "absolutely heartbroken" over his split with Wilde. The source mentioned that there was still a lot of love between them, and Sudeikis hoped there might be a chance to repair their relationship.
By February 2021, Sudeikis was reported to be casually dating British model Keeley Hazell. The source shared with PEOPLE that although the two, who had previously worked jointly on Horrible Bosses 2, were spending time together, Sudeikis was not looking for anything serious.
Legal battle between Jason Sudeikis and Olivia Wilde
In April 2022, Olivia Wilde was served with legal papers from Jason Sudeikis regarding their children's custody while onstage at CinemaCon, creating a highly hyped and embarrassing moment.
Wilde later blamed Sudeikis for deliberately trying to embarrass her and disrupt her presentation, though Sudeikis claimed he had no prior knowledge of the delivery method and had requested a more discreet service.
By August 2022, Wilde sought to dismiss Sudeikis' custody petition filed in New York, which was eventually dropped off due to lack of jurisdiction, keeping the case in California. Amidst their ongoing custody battle, a source reported that while Wilde and Sudeikis no longer communicate directly, both stay focused on guaranteeing the best for their children.
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