Olivia Wilde and Jason Sudeikis' relationship timeline

Where did it all go wrong for Olivia Wilde and Jason Sudeikis? MailOnline looks back at their lengthy 7 year engagement before that shock split and toyboy romance with Harry Styles

  •  The star was at the center of the presentation for her film Don’t Worry Darling in Las Vegas at CinemaCon, when she received legal documents from her ex
  • The very public serving is just the latest in a series of headlines surrounding the former couple 
  • Jason and Olivia met at a Saturday Night Live wrap party in May 2011, when both were recently single 
  • The couple welcomed their first child, a son Otis in 2014, before the birth of their daughter two years later 
  • Olivia cast her now-boyfriend Harry Styles, 28, as the male lead in her second directorial effort Don’t Worry Darling 
  • Two months after the casting, her split from Jason was announced  

In a shock incident, Olivia Wilde was served with custody papers by the father of her children Jason Sudeikis during a live presentation of her new movie on Tuesday.

The star was in the middle of the presentation for her film Don’t Worry Darling in Las Vegas for 4,100 film industry experts at CinemaCon, when she received legal documents from her former partner.

The very public serving is just the latest in a series of headlines surrounding the former couple, whose nine year romance came to a crashing end after Olivia cast 28-year-old heartthrob Harry Styles in Don’t Tell Me Darling.

Split: In a shock incident, Olivia Wilde was served with custody papers by the father of her children Jason Sudeikis during a live presentation of her new movie on Tuesday (pictured during their relationship in 2020)

Jason and Olivia met at a Saturday Night Live wrap party in May 2011, when both were recently single. 

Nine months prior, Olivia ended her eight-year marriage to Italian-American filmmaker Tao Ruspoli and Jason had just divorced screenwriter Kay Cannon, whom he was married to from 2004 to 2010. 

During a 2017 appearance on The Late Late Show With Stephen Colbert, the Horrible Bosses star spilled 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.’

Shock: The star was at the center of the presentation for her film Don’t Worry Darling in Las Vegas for CinemaCon, when she received legal documents from her former partner 

Back then: The very public serving is just the latest in a series of headlines surrounding the former couple, who were together for nine years before their split last year (pictured in 2012)

The actress echoed the thoughts, explaining: ‘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.’

Six months after playing it cool though, the couple were dating and announced their engagement in 2013, after Jason proposed over the holidays.

The couple welcomed their first child, a son Otis in 2014, before the birth of their daughter two years later. 

Speaking to Net-a-Porter’s Porter Edit in February 2016, Wilde explained how she believed becoming a parent with her ex was a stronger commitment for the couple than tying the knot.

Jason and Olivia met at a Saturday Night Live wrap party in May 2011, when both were recently single but played it cool. Six months later though, the couple were dating and announced their engagement in 2013 (pictured in 2013)


Exes: Nine months prior to meeting Jason, Olivia ended her eight-year marriage to Italian-American filmmaker Tao Ruspoli (left) and Jason had just divorced screenwriter Kay Cannon, whom he was married to from 2004 to 2010 (right)

Parents: The couple welcomed their first child, a son Otis in 2014, before the birth of their daughter two years later 

‘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 two managed to balance their thriving careers with parenthood, with Jason supporting Olivia’s shift from actress to director in her 2019 debut Booksmart.

He even made a cameo in the movie, while taking on the primary parent role at the time, with Olivia gushing of working with her then fiancé:

‘There’s still a shorthand that comes from being someone’s closest partner, but I loved being able to just set him free because he’s one of the best improvisers in the world.’

Tribute: Olivia has had the names of her children on her arms and has previously been open about balancing her workload with parenthood alongside Jason

Meeting: Fast forward to 2020 and Olivia was working on casting for her second directorial effort Don’t Worry Darling in which she cast  boybander turned screen star Harry Styles (pictured on set in 2020)

Fast forward to 2020 and Olivia was working on casting for her second directorial effort Don’t Worry Darling.

After firing her original male lead Shia LaBeouf in September 2020 because she has a ‘zero a**hole policy’ and his behavior was ‘off-putting,’ the director landed her dream casting – One Direction boybander turned screen star Harry Styles.

Speaking in Harry’s Vogue cover interview in November 2020, Olivia gushed about her excitement at getting Harry on set, revealing that she and the film’s costume designer, Arianne Phillips, were extra happy to have the star around because of his love for fashion.

Don’t Worry Darling: Speaking in Harry’s Vogue cover interview in November 2020, Olivia gushed about her excitement at getting Harry on set (pictured with Florence Pugh)

‘She [Arianne] and I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style,’ Olivia said.

To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has—truly devoid of any traces of toxic masculinity—is indicative of his generation and therefore the future of the world,’ the star continued.

‘I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.’

Just a few short hours after Olivia praised Harry in print on November 13, her shock split from Jason was reported in PEOPLE Magazine.  

Working hard: Just a few short hours after Olivia praised Harry in print on November 13, her shock split from Jason was reported in PEOPLE Magazine (Olivia pictured on set in 2020)

Olivia and Jason’s relationship 

May, 2011 –  Jason and Olivia meet at a Saturday Night Live wrap party in 2011, when both were recently single after ending their marriages

Jason later recalled he didn’t make ‘any sort of moves’ at the time 

November, 2011 –  The pair start dating after months of friendship

December 2012 – Jason proposes over the holidays

2014 – The couple welcome their first child, a son Otis

2016 – Their daughter Daisy is born with Wilde explaining how she believes becoming a parent with Jason is a stronger commitment for the couple than tying the knot

October 2020 – Olivia starts shooting her second directional effort Don’t Worry Darling, starring new cast member Harry Styles

November 2020 – Jason and Olivia split 

January 2021 –  Harry and Olivia’s romance is confirmed when they are seen holding hands at his agent’s wedding in Montecito, California, on January 3  

The original break-up report cited sources claiming the split was ‘amicable’ and that their two children would remain a ‘priority,’ with a source close to the couple saying: 

‘The split happened at the beginning of the year [2020].’

‘It’s been amicable and they’ve transitioned into a great co-parenting routine. 

‘The children are the priority and the heart of the family’s relationship.’ 

‘They just fell out of love in a romantic way, but still have love towards one another as people,’ a source explained to ET.

‘They consider themselves friends and co-parents first and foremost.’ Another source added, ‘there was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.’

What followed though was conflicting reports as to the timeline of Olivia’s split from Jason and when she started her new relationship with Harry.

The original PEOPLE report claimed that Olivia and Jason broke up ‘at the beginning’ of 2020, but further sources claimed ‘she and Jason were very much together as recently as this fall [2020].’

A report from UsWeekly claimed: ‘Olivia called off the engagement in early November [2020] but only after she already had gotten close to Harry.’ 

Rumours of Harry and Olivia’s romance were confirmed when they were seen holding hands at his agent’s wedding in Montecito, California, on January 3 2021, raising eyebrows over just how quickly she had moved on.

A source claimed to PEOPLE in a January 2021 report, around the time Olivia and Harry went public.

Moving on: Jason, 46, also moved on, embarking on a relationship with his Ted Lasso co-star, British glamour model Keeley Hazell, 35, last year (pictured in June 2021)

‘Jason feels that the timeline that Olivia and Harry would like people to believe – that she and Jason split ages ago, long before she became involved with Harry – is simply not accurate.’

The source added that the trouble began around the start of production on Wilde’s sophomore directorial effort in the fall of 2020.

‘She began filming [Don’t Worry Darling] in September, and by October, he began to get the impression that she wanted out. By November, they’d announced their split.’

The source emphasized ‘that’s how quickly it happened,’ adding that ‘none of it happened until she began filming with Harry.’

In a December 2021 interview with American Vogue the actress referred to the timeline dispute, telling the magazine: ‘It’s obviously tempting to correct a false narrative.’

‘But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you.’

Adding: ‘All that matters to you is what’s real, and what you love, and who you love.’

Jason meanwhile confirmed in a 2021 interview with GQ that the couple split in November 2020, admitting that ‘I’ll have a better understanding of why in a year.’

‘And an even better one in two, and an even greater one in five, and it’ll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle.’

‘That’s an experience that you either learn from or make excuses about,’ he said. ‘You take some responsibility for it, hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it.’

Jason also moved on, embarking on a relationship with his Ted Lasso co-star, British glamour model Keeley Hazell, 35, last year. 

The exes are co-parenting their children, with their current custody arrangements unknown. 

Olivia is currently living in the UK with the singer while Jason films the third series of the comedy drama Ted Lasso.

She has her two children in London while he is working on the Apple TV programme, set in the UK.

‘Ironically, it is Jason’s work that means they can be together,’ said a source, adding that friends are expecting Harry and Olivia to marry.

 Served: The exes are co-parenting their children, with their current custody arrangements unknown amid Olivia’s serving – pictured on Tuesday 

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