Jason Sudeikis and Olivia Wilde's relationship timeline

What started as a meet-cute worthy of its own Hollywood script has been everything but predictable. Jason Sudeikis and Olivia Wilde were the it-couple when they got together back in 2011 after reportedly vibing hard at a Saturday Night Live finale party. Sparks flew, hearts raced, and boom—they were engaged by 2012. A seven-year engagement? Bold move. But it seemed to work... until it didn’t.

Jason Sudeikis and Olivia Wilde’s relationship timeline | Credit: X

When Jason Sudeikis and Olivia Wilde’s relationship bloomed

The couple welcomed two adorable kids—Otis in 2014 and Daisy in 2016—before they called it quits in 2020. And that’s when things got spicy. While insiders initially claimed things were all sunshine and amicable vibes, the real tea started brewing when Olivia began dating none other than Harry Styles. Cue the chaos.

Jason Sudeikis and Olivia Wilde’s relationship timeline | Credit: X

Things went from peaceful co-parenting to a full-on legal showdown. The peak drama? When Jason’s legal team served Olivia with custody papers on stage at CinemaCon in 2022. Yes, mid-speech, in front of a whole crowd. Olivia reportedly felt ambushed and called it "the most aggressive manner possible"—and honestly, it was giving courtroom thriller energy.

Jason Sudeikis and Olivia Wilde’s relationship: From rom-com coded to courtroom custody coded

Their custody war escalated in 2023, with Olivia’s team accusing Ted Lasso actor Jason of trying to “litigate her into debt” (ouch) while battling over where the kids should live—New York or Los Angeles? It was tense, expensive, and honestly, exhausting for everyone watching from the sidelines.

Jason Sudeikis and Olivia Wilde’s relationship timeline | Credit: X

But just like in a good third act redemption arc, things eventually mellowed out. By September 2023, the exes had finally settled the case, with Jason ordered to pay Olivia $27,500 per month in child support. Since then, they have reportedly been nailing the co-parenting game—both living in LA, keeping things civil, and putting their kids first.

Jason Sudeikis and Olivia Wilde spotted hugging each other

Flash-forward to April 2025: Jason and Olivia are spotted hugging at a playground like nothing ever happened. Chatting, laughing, letting Otis and Daisy run around, and giving us a glimpse of what post-drama peace looks like.

Jason Sudeikis and Olivia Wilde’s relationship timeline | Credit: X

Their journey? Part romance, part chaos, full drama—but hey, at least the kids are alright.