Olivia Wilde: How Harry Styles’ girlfriend went from DC elite to controversial ‘Don’t Worry Darling’ director

Olivia Wilde’s star power has been on a steady rise since she appeared as a bisexual bartender on “The O.C.” in 2004 who dated both of Adam Brody and Mischa Barton’s characters.

She recently made headlines for her relationship with co-star Harry Styles — whom she also directed in “Don’t Worry Darling” — her former engagement to Jason Sudeikis, and one super simple salad dressing, but Wilde’s history in the arts is quite literally in her blood.

The 38-year-old actress may now be an award-winning director thanks to a little help from the writers in her family, a name change, and a lot of work. Here’s a look at the life and love of Olivia Wilde, n?e Cockburn.

Written in the Past

Olivia Cockburn was born in New York City and raised in Washington, DC, by journalists Andrew and Leslie Cockburn. Her grandfather was Claud Cockburn, who wrote “Beat the Devil” under the pseudonym James Helvick. He had changed his name after being blacklisted for writing an underground, anti-fascist newsletter.

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She told the New York Observer in 2007 that journalism was “everywhere” in her family, which made her “really critical and analytical.”

In boarding school at the Phillips Academy in Andover, Massachusetts, she began toying with the idea of creating her own pen name and came up with “Wilde” in honor of the Irish poet and playwright Oscar Wilde. Olivia herself had dual citizenship in Ireland and the United States, and spent time studying in Dublin.

“It was meant as an homage to the writers in my family, many of whom created pen names for their careers,” she told Playboy in 2009 of creating her new name in high school. “I have a grandfather who changed his name to James Helvick to write the novel “Beat the Devil,” which got turned into a movie with Humphrey Bogart. I always thought having a pen name was so romantic.”

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She later admitted, “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.”

Princess, Please

Olivia married Italian filmmaker and aristocrat Tao Ruspoli in 2003 when she was 19 years old. Ruspoli is an Italian prince and the son of late Prince Alessandro Ruspoli and actress Debra Berger. She instantly became a real life princess.

“It’s all part of being this lucky person who has been welcomed into an interesting family with a long history,” she told Playboy. “I’m into European history, so it’s exciting to trace our family back to the 14th century and beyond. How many people get to say ‘This castle has been in our family since the 1400s?'”

The House of Ruspoli is originally from Florence, with historical roots dating back to the 13th century. Familial properties include the Palazzo Ruspoli in Rome and the 16th century Castello Ruspoli in Vignanello, Lazio.

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The former couple were engaged at Burning Man and then married on an abandoned school bus in Virginia in front of a handful of witnesses.

“We didn’t want that,” she said. “The bus was the only place we could be completely alone. The wedding was a secret, and we wanted to do it someplace where we could hide with our best friends. It was all about the intimacy of the promise we were making.”

She added, “We were hippies. We lived on that bus for months.”

By March 2011, the fairytale was over and Wilde filed for divorce in a Los Angeles Superior Court citing irreconcilable differences. The divorce was finalized on Sept. 29, 2011.

Saturday Night Love

Shortly after Olivia’s divorce was finalized, she began dating comedian Jason Sudeikis in November 2011.

The “Saturday Night Live” star proposed in January 2013 with little fanfare. Olivia thanked her fans on Twitter for “all the sweet congratulatory love” in addition to the “savvy use of that nifty engagement ring emoticon.” In April 2014, they welcomed their first child, Otis Alexander Sudeikis.

Olivia then gave birth to their daughter, Daisy Josephine Sudeikis, in October 2016. She announced her birth on Instagram and said her baby girl was “born, like a boss, on International Day of the Girl,” October 11.

Despite nearly seven years engaged and a nine-year relationship, Sudeikis and Wilde called it quits in November 2020.

In an August 2021 GQ interview, the “Ted Lasso” star said he still wasn’t really sure what to make of the end of the engagement amid a flurry of speculation she moved on with Harry Styles while they were working on her sophomore directorial picture, “Don’t Worry Darling.”

“I’ll have a better understanding of why in a year,” Sudeikis said, “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 April, Wilde was publicly served custody paperwork seeking to establish New York as their children’s permanent home while speaking in front of more than 4,000 film industry professionals at CinemaCon. Jason denied having any “prior knowledge” of how the papers would be served. She later told Variety, “In any other workplace, it would be seen as an attack.” A judge later ruled in August that California was the children’s home state.

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Adore You

Olivia and Harry were first pictured hand in hand walking together in January 2021 before the “Watermelon Sugar” singer served as the officiant at his agent Jeff Azoff’s wedding in Montecito, Calif.

Before going public with their relationship, Wilde told Vogue in December that she was thrilled when Harry signed on to star opposite Florence Pugh in her new movie.

“She 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 of celebrating with costume designer Arianne Phillips. “And this movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that he is so enthusiastic about that element of the process–some actors just don’t care.”

“To me, he’s very modern,” Wilde said of Styles,” 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. 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.”

Their love certainly flourished off set, too, as Olivia has been Harry’s biggest supporter as he went on tour around the world. She was able to attend a few of his gigs in person, but has been seen sporting his merch around town.

Earlier this week, Wilde rocked a “Harry’s House” sweatshirt, a nod to his third studio album which was released in May.

The “Booksmart” director has also been seen carrying gear from Harry’s concerts to the gym and while shopping.

In addition, Olivia recently showed support for his latest business venture, Pleasing. The beauty brand, which launched almost a year ago, features nail polishes, skin care products, makeup and apparel.

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The Salad Dressing

Amid accusations waged by a former family nanny that Sudeikis was blindsided by Wilde’s relationship with Styles, Wilde gave Instagram fans a little taste of the juicy gossip. Both Olivia and Jason vehemently deny the allegations.

One of the many revelations recently made by the caretaker was how upset Sudeikis became upon hearing that Olivia was bringing a salad with her “secret dressing” to Styles while she was still dating the “Ted Lasso” star, according to DailyMail. Sudeikis, so distressed that she was departing with the dressing, then “went outside and lay under her car so she wouldn’t leave.”

The former couple responded in a joint statement shared to Fox News Digital, “As parents, it is incredibly upsetting to learn that a former nanny of our two young children would choose to make such false and scurrilous accusations about us publicly.”

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They added, “Her now 18-month-long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex,” the statement said. “We will continue to focus on raising and protecting our children with the sincere hope that she will now choose to leave our family alone.”

But Wilde played into the hearsay days after by sharing a photo of page 177 from Nora Ephron’s 1983 autobiographical novel, “Heartburn,” which is based on her own failed marriage and subsequent divorce from her second husband, journalist Carl Bernstein, due to infidelity.

Olivia posted the page of the book to her stories on her Instagram account without any commentary.

“Mix 2 tablespoons Grey Poupon mustard with 2 tablespoons good red wine vinegar. Then, whisking constantly with a fork, slowly add 6 tablespoons olive oil, until the vinaigrette is thick and creamy; this makes a very strong vinaigrette that’s perfect for salad greens like arugula and watercress and endive,” the excerpt read.

The dressing became such a viral sensation that Grey Poupon announced a chance for fans to win a limited-edition “Don’t Worry Dijon” jar in an Instagram contest.

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