A Complete Timeline of Jason Sudeikis and Olivia Wilde's Long-Term Relationship

With Jason Sudeikis' attorneys serving Olivia Wilde with custody papers at CinemaCon, let's find out more about their long-term relationship.

Allison DeGrushe - Author

Aug. 10 2022, Updated 7:45 p.m. ET

Jason Sudeikis and Olivia Wilde in December 2019.
Source: Getty Images

While on stage at CinemaCon 2022, Olivia Wilde was served with custody papers.

Before presenting the trailer of her sophomore feature film, Don’t Worry, Darling, a spectator handed a cryptic manila envelope labeled "personal and confidential" to Olivia, which contained legal documents from her former fiancé, Jason Sudeikis. If you're hoping to get more insight into the current drama, here is a complete timeline of their long-term relationship.

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May 2011: Jason Sudeikis and Olivia Wilde meet at an 'SNL' wrap party.

Both recently divorced and single, Jason and Olivia first met at the Saturday Night Live Season 36 wrap party. Regarding the encounter, Jason told Stephen Colbert in 2017 that he "came off looking a lot cooler" than he really is because mutual friends informed him she was dating someone. As a result, he didn't "make any sort of moves" until months later.

Jason Sudeikis and Olivia Wilde in October 2012.
Source: Getty Images
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November 2011: The famous pair officially start dating.

Nearly six months after their initial meeting, Jason's busy schedule cleared up and Olivia stopped seeing someone else. As a result, the pair officially began dating, and shortly after, the couple took their romance to new heights.

January 2013: Jason and Olivia confirm their engagement.

In January 2013, a source close to Jason and Olivia spoke to People and confirmed they were engaged. The outlet reported that the SNL alum proposed shortly after the holidays, noting that they were "so excited" to spend the rest of their lives together.

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Jason Sudeikis and Olivia Wilde at TIFF in September 2013.
Source: Getty Images

August 2013: The couple appear in their first film together.

Jason and Olivia appear in their first film together, Drinking Buddies. The dramedy centers around co-workers Kate (Wilde) and Luke (Jake Johnson), with Jason making a brief appearance as Gene Dentler (credited as Gene Dentler playing "Himself").

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October 2013: Olivia is pregnant with their first child.

In late October 2013, a rep for Olivia confirmed to Us Weekly that she and Jason were expecting their first child. At the 86th Annual Academy Awards, the soon-to-be mother flaunted her growing baby bump on the red carpet.

Olivia Wilde shows off her baby bump at the 2014 Oscars.
Source: Getty Images
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April 2014: Jason and Olivia welcome their son, Otis Sudeikis.

On April 20, Jason and Olivia welcomed their first child, a son named Otis. Olivia shared the news on Twitter, announcing that "Otis Alexander Sudeikis has left the building! (I'm the building)," alongside a photo of her cradling her newborn son.

April 2016: Jason jokes he will marry Olivia once "weed is legal in every state."

Although Jason popped the question in 2013, he joked three years later that he and Olivia wouldn't walk down the aisle anytime soon. During an appearance on Watch What Happens Live With Andy Cohen, a viewer asked when they were getting married.

"I know this isn’t my mom because my mom’s in the audience,” Jason quipped via Us Weekly. "I mean, I believe we won’t get married until weed is legal in every state, gosh darn it!”

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May 2016: Olivia sports a baby bump at the Met Gala.

On April 18, Olivia took to Instagram to announce she was pregnant with her and Jason's second child.

The actress posted a photo of her and Otis holding their bellies, with the caption that read, "Matching baby bumps." A few weeks later, Olivia arrived at the 2016 Met Gala and posed on the carpet with her fellow pregnant friend, Emily Blunt.

Olivia Wilde and Emily Brunt both rock baby bumps at the Met Gala in May 2016.
Source: Getty Images
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October 2016: Jason and Olivia welcome their second child, Daisy Sudeikis.

On Oct. 11, 2016, Olivia gave birth to her and Jason's second child, a daughter named Daisy. Five days later, the Meadowland actress shared the news on Instagram with a photo of the new member of the Sudeikis-Wilde clan.

"There goes the neighborhood," Olivia penned. "Daisy Josephine Sudeikis. Born, like a boss, on #internationaldayofthegirl."

March 2019: Jason supports Olivia at the SXSW premiere of 'Booksmart.'

Though the engaged pair continued to keep their romance alive with two kids, nothing makes our hearts flutter more than Jason standing by his fiancée's side at the SXSW premiere of Booksmart. The film, which garnered critical acclaim, was Olivia's directorial debut. Additionally, Jason played a part in the movie, starring as Principal Jordan Brown.

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Jason Sudeikis and Olivia Wilde at the SXSW world premiere of 'Booksmart.'
Source: Getty Images

November 2020: The couple end their seven-year engagement amidst rumors that Olivia Wilde cheated on Jason.

Then in 2020, we all learned that love isn't real.

On Nov. 13, People reported that Jason and Olivia ended their seven-year engagement. A source close to the pair revealed that "the split happened at the beginning of the year," and they quickly "transitioned into a great co-parenting routine."

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Since then, Olivia has been dating English singer and actor Harry Styles. The pair met while filming Olivia's second feature film, Don't Worry, Darling, and many have speculated that Olivia cheated on Jason with Harry. According to sources, co-star Florence Pugh was bothered by "seeing Olivia and Harry all over each other on set ... as Olivia was still with Jason when she first hooked up with Harry."

As for Jason, he's been dating his Horrible Bosses 2 and Ted Lasso co-star Keeley Hazel since 2021.

April 2022: Olivia Wilde is served child custody papers while on stage at CinemaCon.

While promoting Don't Worry, Darling at CinemaCon on April 26, an individual approached the stage and slid a manila envelope marked "personal and confidential" toward Olivia.

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Olivia Wilde was served custody papers on stage at CinemaCon 2022.
Source: Getty Images

After asking if it was for her, the 38-year-old director looked over the paperwork before resuming her presentation. The following day, Deadline reported the mysterious envelope contained custody papers from her former fiancé. Olivia and Jason had been arguing about where to permanently raise their kids, with him wanting to settle in New York and Olivia wanting to relocate to London to be closer to Harry Styles.

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According to the Los Angeles Times, Jason was furious with the spectacle.

"Mr. Sudeikis had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved," reads a statement provided to the Los Angeles Times. "He would never condone her being served in such an inappropriate manner."

However, Olivia appears to believe the action was intentional. In court documents obtained by the Daily Mail in August 2022, Olivia said, "Jason's actions were clearly intended to threaten me and catch me off guard. He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible."

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