Olivia Wilde: who is Harry Styles’ girlfriend, age, is she pregnant - when did she date Jason Sudeikis?

The Don’t Worry Darling director had previously been engaged to Ted Lasso star Jason Sudeikis from 2013 to 2020

Harry Styles is one of the biggest names in the world right now and thus public speculation surrounding his relationships are to be somewhat expected - and his ongoing relationship with Olivia Wilde is one that has invited much scrutiny.

Earlier this year, Wilde was served legal papers on behalf of her ex-fiance Jason Sudeikis whilst appearing at CinemaCon to promote her upcoming film Don’t Worry Darling, which stars Styles in one of the lead roles, opposite Florence Pugh (Midsommar, Little Women).

This is everything you need to know.

Who is Olivia Wilde?

Wilde is an American actress and filmmaker who many will recognise as 13 in the medical drama House in which she starred opposite Hugh Laurie (The Night Manager, Veep) from 2007 to 2012.

Wilde, whose real name is Olivia Jane Cockburn, was born in New York on 10 March 1984, and grew up in Georgetown in Washington, D.C. She spent her summers in Ardmore in Ireland as her father is Irish.

She attended private school Georgetown Day School and then boarding school Phillips Academy in Massachusetts which she graduated from in 2002.

Olivia Wilde at the 3rd Annual Hollywood Critics Awards at Taglyan Complex on January 09, 2020 in Los Angeles, California (Photo by Rachel Luna/Getty Images)

After moving to Dublin to study acting at the Gaiety School of Acting, Wilde changed her name in order to create her own identity away from her family’s name - her mother, Leslie Cockburn (née Redlich) was an American producer on 60 Minutes and a journalist, and her father was also a journalist and editor of Harper’s Magazine.

Speaking to the Observer in 2007, she said: “My mother thought it was a good idea for me as well, so I could have my own identity outside of my family. She suggested I pick something Irish and something that I’d always be inspired by.

“At the time, I was doing The Importance of Being Earnest - I was playing Gwendolyn, and I was so in love with it.

“Oscar Wilde is someone who I respect for so many reasons - a revolutionary, a comedian and a profound thinker. I had all these reasons - but what I didn’t foresee is that people would think of it as a sexy adjective.

“So now it’s got a pornographic quality I never considered.”

Olivia Wilde accepting the Hollywood Breakthrough Director Award onstage during the 23rd Annual Hollywood Film Awards at The Beverly Hilton Hotel on November 03, 2019 in Beverly Hills, California (Photo by Kevin Winter/Getty Images for HFA)

Wilde has appeared in other on screen roles in films and TV shows such as The O.C, Bojack Horseman, Portlandia, Year One, Tron: Legacy, Cowboys & Aliens, In Time, The Incredible Burt Wonderstone, The Lazarus Effect, Her and Rush.

She made her directorial debut in 2019 with the film Booksmart, starring Beanie Feldstein (American Crime Story, What We Do in the Shadows) and Kaitlyn Dever (Unbelievable, Justified), and is currently directing Don’t Worry Darling in which she will also play a supporting role.

How long were Olivia Wilde and Jason Sudeikis together - when did they break up?

Prior to meeting, both Wilde and Sudeikis had been married and subsequently divorced.

At just 19, Wilde married Italian filmmaker and musician Tao Ruspoli. She filed for divroce on 3 March 2011, citing “irreconcilable differences”, with the divorce itself finalised on 29 September 2011.

Sudeikis had married screenwriter Kay Cannon in 2004, after having already been together for five years. They separated in 2008 and finally divorced in February 2010.

Olivia Wilde and Jason Sudeikis at the 9th Annual Veuve Clicquot Polo Classic in Los Angeles, California, on October 6, 2018 (Photo by LISA O’CONNOR/AFP via Getty Images)

Wilde and Sudeikis began dating in 2011 after meeting at a Saturday Night Live afterparty.

Appearing on The Late Late Show with Stephen Colbert in 2017, Sudeikis talked about his first interaction with Wilde.

He said: “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.

“I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races.”

Olivia Wilde and Jason Sudeikis at the 2018 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 4, 2018 in Beverly Hills, California (Photo by Dia Dipasupil/Getty Images)

Wilde told Allure that, after bumping into each other a number of times after meeting at the afterparty, one of her friends approached Sudeikis and said: “This is Olivia’s number. Use it.”

“That was the beginning,” Wilde said.

In Marie Claire’s April 2013 cover story, Wilde described Sudeikis as “the great love of my life” and opened up about how, at the time, she wasn’t really looking for love.

She said: “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.”

The pair announced their engagement in 2013 and during the time of their engagement welcomed their two children into the world - son Otis, born in 2014, and daughter Daisy, born in 2016.

Jason Sudeikis and Olivia Wilde at the IFP’s 29th Annual Gotham Independent Film Awards at Cipriani Wall Street on December 02, 2019 in New York City (Photo by Jemal Countess/Getty Images for IFP)

The couple never made it down the aisle and, according to Sudeikis in a 2021 interview with GQ, they split in November of 2020.

A source reportedly told People magazine at the time that the pair had ended their years long engagement “amicably”.

They said: “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.”

Is she dating Harry Styles?

News of the end of Wilde and Sudeikis’ relationship was confirmed when she was seen holding hands with Harry Styles in January 2021. According to Sudeikis in his GQ profile, he didn’t even have clarity about the end of their relationship at that point yet.

He said: “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.”

In September 2020, Wilde cast Styles in her upcoming film Don’t Worry Darling, replacing Shia LaBeouf.

Harry Styles performing on NBC’s Today at Rockefeller Plaza on February 26, 2020 in New York City (Photo by ANGELA WEISS/AFP via Getty Images)

Wilde was interviewed as part of Styles’s Vouge cover story, which was published in November 2020, in which she said that she and Don’t Worry Darling costume designer Arianne Phillips “did a victory dance” when Styles was cast.

She said: “[Phillips] 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.”

After pictures of her and Styles holding hands surfaced online in January 2021, a source reportedly told People: “They were in Montecito, California this weekend for a wedding.

“They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks.”

Another source also told Entertainment Tonight: “Olivia and Harry are together for long days on set and have gotten to know each other really well, so it’s all very organic.

“[Wilde] wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.”

In February 2021, Wilde shared a picture of Styles on her Instagram as Don’t Worry Darling filming came to an end.

In the caption, she wrote that Styles “infused every scene with a nuanced sense of humanity” and that he “jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards”.

In July 2021, the two were photographed kissing and getting close on a boat in Italy, and in September 2021, Wilde was seen supporting Styles at the opening night of his Love on Tour show in Vegas.

Over the course of their relationship, there has been criticisms regarding the age gap between the two, with Wilde 10 years Styles’ senior - Wilde is 38 and Styles is 28.

Without mentioning Styles directly, Wilde appeared to address the scrutiny in a December 2021 interview with Vogue, where she said: “It’s obviously really tempting to correct a false narrative.

Olivia Wilde speaking onstage at Booksmart Q&A during the 22nd SCAD Savannah Film Festival on October 29, 2019 at Trustees Theater in Savannah, Georgia (Photo by Cindy Ord/Getty Images for SCAD)

“But I think what you realise is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love.”

She added: “In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us.

“I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that.”

Earlier this year, in February 2022, Wilde and Styles were spotted together in London.

Is she pregnant?

Despite much Twitter speculation, Wilde is not confirmed to be pregnant. In the run up to the release of Styles’ new album, Harry’s House, which dropped on Friday 20 May, social media rumours took over the internet which claimed that the former One Direction singer was going to be a father.

The rumours appear to have been sparked by a picture shared on Twitter which, at an angle, may have possibly hinted at the slightest beginnings of a baby bump. However, it has since become evident that Wilde is not expecting any time soon.

Neither Wilde or Styles have commented on the pregnancy rumours.

What happened at CinemaCon?

Wilde was reportedly served with legal papers on behalf of ex Sudeikis whilst on stage to promote her new film earlier this year.

She had been at CinemaCon in Las Vegas at a presentation for her upcoming thriller, called Don’t Worry Darling which stars Harry Styles (Dunkirk, Eternals) and Florence Pugh (Little Women, Midsommar), when she was given a brown envelope.

According to US media outlets, a person approached the stage from the seated section and slid the envelope, which was marked “private and confidential”, across the front of the stage to Wilde, who then opened it.

Director and actress Olivia Wilde speaking onstage during CinemaCon 2022 presentation, April 26, 2022 in Las Vegas, Nevada (Photo by Greg Doherty/Getty Images)

Per Deadline, the envelope reportedly held custody documents relating to the two children Wilde shares with the Ted Lasso star.

A source for 46-year-old Sudeikis told US showbiz outlet Variety: “Papers were drawn up to establish jurisdiction relating to the children of Ms Wilde and Mr Sudeikis.

“Mr Sudeikis had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved, and he would never condone her being served in such an inappropriate manner,” the source added.