From Saturday Night Live to serving court papers: Jason Sudeikis and Olivia Wilde¡¯s timeline is wilder than any rom-com
Jason Sudeikis and Olivia Wilde¡¯s love story went from rom-com cute to legal drama real fast. From meeting at an SNL party to a dramatic custody battle and awkward CinemaCon moments, their co-parenting saga has had more twists than a Netflix thriller. Now? Hugging it out like pros in LA.
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¡ªthey 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¡ªOtis in 2014 and Daisy in 2016¡ªbefore 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"¡ªand 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¡ªNew 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¡ªboth 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¡ªbut hey, at least the kids are alright.
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