People often ask How long did Olivia Wilde and Jason Sudeikis date? Olivia Wilde and Jason Sudeikis dated for just over 7 years, from November 2011 when they first began seeing each other, to November 2020 when they ended their engagement and relationship.
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Olivia Wilde and Jason Sudeikis charmed Hollywood and fans alike with their sweet relationship that spanned over seven years.
They always appeared incredibly affectionate and supportive of one another at events and in interviews, leading the public to believe they were one of the strongest couples in the entertainment industry.
However, behind the lovely Instagram posts and cute red carpet photos, there were reportedly issues bubbling under the surface towards the end.
This in-depth blog post will take you through the full timeline of Wilde and Sudeikis’s romance, from their meet-cute at an SNL finale party in 2011 to their difficult breakup in November 2020.
We’ll cover the key moments in their love story – like getting engaged, having two children, and ultimately deciding to go their separate ways.
Additionally, we’ll explore what both stars have been up to since ending their long-term relationship.
Grab some popcorn and get comfy as we dive into Olivia and Jason’s love affair!
The Early Days: First Meeting and Start of Their Romance
First Meeting at SNL Finale Party
Back in May 2011, Olivia Wilde was fresh off separating from her ex-husband, filmmaker Tao Ruspoli.
Newly single, she attended a Saturday Night Live finale party that same month. Little did she know she was about to meet her future fiancé, SNL alum Jason Sudeikis.
Sparks evidently flew instantly between the pair. Only a few months later, they officially began dating. While Wilde and Sudeikis have never divulged too many details about their first encounter, it clearly made quite the impact!
How Long Did Olivia Wilde and Jason Sudeikis Date
By November 2011, Wilde and Sudeikis’s friendship had taken a romantic turn. The two were spotted holding hands in New York City, confirming rumors that they were now an item.
Up until going public with Sudeikis, Wilde had never spoken much about her love life in interviews. But she seemed utterly smitten with Jason from the start. Just six months into dating, she Tweeted the below about her new beau:
“Real men wear jewelry. My fiancée wears the one ring that rules them all.”
Cute Tolkien reference aside, it was clear Olivia was head-over-heels for Jason. As of June 2012, she couldn’t stop gushing over him in magazine profiles. She discussed: in a Marie Claire interview:
“I am so in love, just about to the point where my head explodes…I’m very happy.”
She echoed similar sentiments to Glamour, telling them:
“I’m happier than I’ve ever been. I’m flourishing!”
So in those first months as an official couple, things were all sunshine, rainbows, and positive vibes between Olivia and Jason. Their friends noted their effortless chemistry and similar senses of humor. Before long, Jason was ready to put a ring on it!
III. Getting Serious: Engagement and Growing Family
The January 2013 Marriage Proposal
After around a year together, Jason popped the question over the holidays [2]. In January 2013, Olivia flashed her new engagement ring while speaking on stage at that year’s Golden Globes.
Months later in her Glamour interview, she shared sweet insights into the proposal itself:
“I was just weeping and weeping, but I was so shocked. I had no idea! He surprised me at Christmas…All I could keep saying was, ‘Are you sure?’ My dad walked in and was like, ‘Did you say yes?’ Jason said, ‘She is so shocked I don’t think she said yes yet.'”
Despite having some initial disbelief, she did indeed enthusiastically accept. And thus began their years-long engagement leading up to what they hoped would be a walk down the aisle.
Expand Their Family With Two Children
About a year after getting engaged, Olivia gave birth to their first child – a son named Otis Alexander Sudeikis – on April 20, 2014. Tragically, this joyful time coincided with the loss of Jason’s dear friend and comedy partner, Harris Wittels, to a drug overdose. But despite the grief, Otis’s arrival appeared to lift his father’s spirits.
Flash forward to October 2016, and baby number two made her debut. Sweet little Daisy Josephine Sudeikis joined big brother Otis on October 11, 2016. Now a family of four, Olivia and Jason seemed to be thriving during their time as partners and parents.
On what appeared like endless blissful days with the kids, Wilde gushed in 2017:
“Being a parent is the most completely humbling experience…That cliché about children keeping you young and youthful is so real.”
For his part, Jason has always spoken incredibly highly of Olivia’s parenting style. Shortly after Daisy’s birth, he bragged to Stephen Colbert:
“Olivia does a lot of the hard work, to be fair. She keeps those kids, those little Sudeikises, in line.”
But somewhere along the way, unseen issues crept into their storybook romance and family unit.
The Breakup: Ending Their 7+ Year Romance
Remaining Amicable Despite the Split
The news broke in November 2020 that Wilde and Sudeikis were ending their seven year engagement. And it reportedly blindsided everyone close to the formerly beloved duo. Those in their inner circle regarded them as “the closest couple.”
Publicly, though, both Olivia and Jason framed the breakup as completely drama-free. In January 2021, Jason told GQ Magazine:
“I’ll have a better understanding of why [the split happened] in a year, and an even better one in two, and an even greater one in five.”
He seemed stunned by the split, as did their friends. Especially since Olivia was spotted soon after their separation canoodling with Harry Styles.
Her moving on so quickly reportedly “hit Jason hard.” He even still wore his “To Olivia” ring months after the breakup.
But when asked about Wilde in that same GQ interview, Sudeikis only had kind things to say about his ex and co-parent:
Focus on Co-Parenting
Both Olivia and Jason emphasized post-split that their main priority was raising Otis and Daisy peacefully. Jason told GQ he leans on wisdom from his community to navigate co-parenting. Adding:
“It’s not about being the ‘here’ parent or the ‘there’ parent. It’s just: Are you available and are you accountable?”
For her part, Olivia tries to maintain a positive co-parenting dynamic by keeping arguments away from the kids:
“The only way I was able to get through it was to think, ‘What would serve them best?’ Whether consciously or subconsciously, the adults around little ones tend to project their anxieties onto them,” she told Marie Claire.
“As a fierce protector of them, I worked very hard — even in moments when I didn’t feel like it — to be detached from the toxicity and chaos and anger.”
Despite seeming well-matched initially, Olivia and Jason evidently faced challenges further into their romance. But their mutual devotion to Otis and Daisy remained steadfast.
Reflecting Back on Their Time Together
The Good Times
Goofy and outgoing, Jason seemed to help bring Olivia out of her shell during their early days as a couple. Describing herself as an introvert, she shared with Marie Claire:
“I’m so grateful that he came along because there were moments where I could not actually see myself being someone’s mom.
And then I met him and was like, ‘Oh, I get it. I understand. You give me confidence that I can do this.’ Jason has really made me laugh about parenting.”
Laughing often around one another, comfortable silence between them – their natural chemistry and friendship provided the sturdy foundation for the relationship.
Jason supported Olivia whole-heartedly as she launched her directing career with 2019’s smash hit *Booksmart*.
And Olivia showed up at every one of Jason’s SNL hosting gigs – even when nine months pregnant! They were the epitome of CoupleGoals for so long.
Signs of Trouble Behind the Scenes?
Rumors of issues between the two picked up steam around late 2019/early 2020. Olivia began spending long stretches of time working on projects in London. Tabloids alleged her distance took a toll on their romance.
Then when filming her psychological thriller *Don’t Worry Darling* in 2020, Olivia met now-boyfriend Harry Styles. Jason was still living in Los Angeles full-time with Otis and Daisy during this period.
So could this physical separation mixed with new outside romantic prospects have torpedoed Olivia and Jason’s relationship?
Some sources claimed Olivia simply felt she and Jason fundamentally wanted different things. Others pinpointed Jason’s desire to stay based in LA near SNL as the breaking point.
Ultimately, we may never know all the personal details behind their uncoupling. But looking back, early 2020 does appear to be the beginning of the end.
Where Are They Now
Olivia Wilde’s Dating Life Post-Split
Mere weeks after splitting from Jason, Olivia made major headlines in January 2021. She was photographed holding hands with pop icon and actor Harry Styles at his manager’s wedding.
Harry had just starred as the lead in Olivia’s sophomore directorial film *Don’t Worry Darling*. So likely their friendship turned romantic on-set.
Three years strong now, Olivia seems extremely content with Harry. She splits time between living in LA and NYC to spend as much time together as they can.
In interviews, Olivia doesn’t share much on her current relationship. But she does continue praising her ex Jason’s parenting skills frequently.
It’s clear those positive co-parenting vibes are still going strong.
Jason Sudeikis’ Life Today as a Single Dad
Residing primarily in Brooklyn since parting ways with Olivia, Jason continues starring on television’s hit show *Ted Lasso*.
He conveyed feeling burnt out from SNL’s hectic schedule towards the end of his long-term run on the sketch series.
So shifting his focus to Otis and Daisy has been a top priority the past few years. That said, he does balance dad duty with his booming acting career.
In summer 2022, Jason was first linked to model Keeley Hazell. England-born Keeley has served as Jason’s close pal for years. She also briefly appeared on Horrible Bosses 2 with Jason back around 2014.
So it’s likely more of a casual, longtime friends situation than full-blown romance. But either way, Jason does seem to be dipping his toes back into dating.
All the while, he never misses a school play, dance recital, or sports game for his cherished kiddos. Their happiness is his main objective as he guides them through childhood.
Parting Thoughts
And so concludes the multi-year saga of Olivia Wilde and Jason Sudeikis as a celebrity power couple. They shared countless smiles, laughs, and tender moments throughout their seven year engagement and decade-long friendship.
Hitting snags towards the latter part of the relationship, they nonetheless prioritize amiability and unity for Otis and Daisy’s wellbeing.
Perhaps one day years down the road, Olivia and Jason will each gain enough clarity to fully understand why their picture-perfect romance ultimately crumbled.
For now, though, they’re focused on finding their individual paths post-breakup and putting their precious children first.
Both stars will undoubtedly continue conquering Hollywood in the director’s chair and on the stage and screen.
All the while guiding young Otis and Daisy through these formative early chapters. And that shared devotion shows despite relationship struggles, these two are and always will be family.
