Olivia Wilde and Jason Sudeikis had a low-key Hollywood romance that all began during a late-night Saturday Night Live afterparty.
Wilde and Sudeikis met in 2011 following their respective divorces. The Booksmart director was married to Italian-American filmmaker Tao Ruspoli from 2003 to 2011, while the Saturday Night Live alum was married to screenwriter and filmmaker Kay Cannon from 2004 to 2010.
During a 2017 appearance on The Late Late Show With Stephen Colbert, the Horrible Bosses star dished on his first interaction with Wilde.
“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,” he recalled at the time. “I was just very, very busy with other things.”
The former House actress, for her part, opened up how her separation from Ruspoli led her to Sudeikis in Marie Claire’s April 2013 cover story. “I had grown up with Tao; we had just drifted. I felt I had something to prove,” she explained at the time. “If you fall off a horse, you get back up. I am not a quitter. I hung on for as long as possible, until it was more hurtful to stay.”
Wilde continued, “I’m so grateful for the pain and the heartbreak. It gave me the courage to leave and brought me to the great love of my life.”
The Tron: Legacy star also told the publication that she wasn’t necessarily looking for love when she first met Sudeikis, adding, “I was just learning to be by myself; I’d been divorced nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls–t.”
Wilde and Sudeikis announced their engagement in 2013. They are now parents of son Otis and daughter Daisy.
Speaking to Net-a-Porter’s Porter Edit in February 2016, Wilde explained how she believed becoming a parent alongside Sudeikis was a stronger commitment for the couple than tying the knot.
“We are seriously connected,” she said. “Before you have a child, marriage is the ultimate commitment and promise to one another, and then once you have a child, it’s like, ‘Oh, we’re committed and promised already.’”
The longtime couple’s romance came to an end in 2020, when Us Weekly confirmed that they had called off their engagement.
Scroll down to see a complete timeline of Wilde and Sudeikis’ romance throughout the years.