In a video released by the Daily Mail, Jason Sudeikis, the Ted Lasso star, was spotted beside an unidentified woman in the Los Feliz area of L.A. The actor, 49, and the brunette woman were dressed casually. Sudeikis was previously engaged to actress and director Olivia Wilde. The publication suggests that the pair may have been on a date, though no official statement has been shared.

PEOPLE published an article on January 12, 2013, where they learned that Sudeikis was serious about his relationship with Olivia Wilde and had proposed to her shortly after their holidays. The couple split ways in 2020 after nine years of dating.

Jason Sudeikis's Dating History Explored:

Kay Cannon :

Sudeikis met writer-director Kay Cannon in the late 1990s while performing improv in Chicago. The couple dated for several years before marrying in 2004. Sudeikis was later accepted as a cast member for Saturday Night Live. The couple eventually separated in 2008, finalizing their divorce two years later. Despite the split, the two have remained friendly.

Dating rumors between Jason Sudeikis And January Jones:

It kicked off in July 2010 after the two were spotted at an ESPY after-party. More sightings followed on set and later at lunch in LA, which further fueled the rumors. Sudeikis later confirmed the relationship during an interview on Lopez Tonight, as reported by HuffPost.

But by January 2011, it was over. PEOPLE reported that long distance made things tough for the couple.

Olivia Wilde:

Jason Sudeikis met Olivia Wilde at a Saturday Night Live after-party in May 2011. She later recalled the moment on The Howard Stern Show, explaining that she was actually there as a date of someone else when Sudeikis approached her and said,

“Whatever you’re looking for, you don’t need it.”

According to Wilde, Sudeikis claimed it wasn’t a pick-up line, and despite their moment, he left the party without asking for her number. They kept crossing paths at industry events over the next few months but failed to connect.

Wilde then has her male friend slip her number to Sudeikis, and not long after, they had their first date at a cozy NYC restaurant. By the end of that night, she later said, she was already falling for him.

The two officially started dating in November of that year.

During the nine-year relationship, the couple welcomed two children, son Otis and daughter Daisy, before announcing their separation in 2020. Since then, their breakup has been followed by a custody battle that has received widespread media coverage. While Sudeikis has remained largely private, he hinted about the emotional toll of the split.

Wilde opened up on an episode of The Kelly Clarkson Show. She shared that her kids are her priority.

"That's what it is. It's as long as they're happy and they're healthy then, my ex and I, we agree on that. They are everything to us."

In an interview with Vanity Fair , Wilde shared that Sudeikis had equal custody, and she trusts him to be a great parent.

“When they are with their father, I trust him to be a great parent. So when they’re not with me, I continue to live my life.