Olivia Wilde and Jason Sudeikis's Relationship Timeline

Olivia Wilde and Jason Sudeikis might have recently ended their engagement, but a lot has happened over the course of their nine-year relationship—seven of which were spent as fiancés! From the birth of their children to their jokes on when they would eventually tie the knot, here is a complete timeline of Olivia Wilde and Jason Sudeikis's relationship.

• Jason Sudeikis and Olivia Wilde first met in 2011 and began dating a few months later.
• They got engaged over the holidays in 2012 but didn't confirm the good news until January of 2013.
• In 2014 and 2016, the couple gave birth to two children: a son, Otis, and a daughter, Daisy, respectively.
• After a seven-year engagement, Olivia and Jason ended their relationship in November 2020 but continue to co-parent.

May 21, 2011: That's a Wrap

When Olivia and Jason first met at the season 36 wrap party of "Saturday Night Live," both were recently single. Nine months prior, Olivia ended her eight-year marriage to Italian-American filmmaker Tao Ruspoli and Jason had just divorced screenwriter Kay Cannon, whom he was married to from 2004 to 2010. “I actually came off looking a lot cooler than I really am because I had heard through the grapevine, through mutual friends that weren’t exactly her best girlfriends, that would report back, ‘Oh, you know, I think she’s dating someone,’ so I didn’t make any sort of moves,” Jason recalled to Stephen Colbert in 2017. “I was just very, very busy with other things.”

November 2011: An Official Couple

But by November of that year—six months after first meeting—Jason and Olivia began dating.

December 2012: A Holiday Proposal

While no one knows exactly how the proposal went down, Jason popped the question to Olivia over the holidays after a year of dating. The actor duo, however, didn't reveal the exciting milestone until after the New Year.

August 23, 2013: Co-Stars on the Silver Screen

The engaged couple made starred in their first film together in 2013. While the actress played the lead role in Drinking Buddies, Jason did make an appearance in the rom-com.

October 27, 2013: A Growing Baby Bump

On October 27, 2013 sources confirmed to several publications that Olivia was pregnant with her first child with Jason Sudeikis. From then on, the director flaunted her growing baby bump on several red carpets—including the Oscars in 2014!

April 20, 2014: Otis Sudeikis Is Born

Olivia and Jason gave birth to their first child, a son named Otis, on April 20, 2014.

April 14, 2016: When Is the Wedding?

Engaged for nearly three-and-a-half years at this point, Jason joked to Andy Cohen when he would eventually get married on "Watch What Happens Live." He told the host, "I mean, I believe we won’t get married until weed is legal in every state.”

April 18, 2016: Expecting Baby Number Two

Olivia turned to Instagram to announce her second pregnancy with fiancé Jason in 2016. "Matching baby bumps," she wrote alongside a photo of her and two-year-old son Otis.

October 11, 2016: Daisy Sudeikis Is Born

And on October 11, 2016, the couple welcomed their second child and first daughter, Daisy Sudeikis.

February 26, 2018: All About Date Nights

The secret to keeping romance alive with two young kids? For Olivia and Jason, it is date night. The actress told Us Weekly in 2018, "We prioritize date night. We go out and have a lot of fun. We were both really social people when we met, and we didn’t want to give that up when we became parents, so we’re really consistent about our time with them, but we also prioritize a couple of date nights a week.”

March 24, 2018: A Rare Family Outing

The Hollywood couple made a rare appearance as a family of four during the March For Our Lives event in Los Angeles on March 24, 2018.

March 10, 2019: Directorial Debut

As Olivia made her directorial debut for the 2019 film Booksmart, Jason stood by her side at the movie's premiere at the SXSW festival.

November 13, 2020: Ending the Engagement

On November 13, 2020, news broke that the couple had ended their seven-year engagement. However, a source told People that the split occurred months prior, saying, "The split happened at the beginning of the year. It's been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship."

November 14, 2020: Putting the Children First

A day after their breakup was revealed, Olivia shared a photo of her two children on Instagram and called them "My everythings."