Olivia Wilde’s Boyfriend: Learn About Harry Styles & Jason Sudeikis – Hollywood Life

Olivia Wilde’s Boyfriend: Everything To Know About Reported Ex Harry Styles & Ex Jason Sudeikis

Olivia and Jason were together for nearly 10 years before they split up. She then moved on to Harry Styles, but they pair split after nearly 2 years. Read about the relationships here.

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  • Olivia Wilde and Jason Sudeikis were in a nearly decade-long relationship that produced two children
  • Olivia started dating Harry Styles after she met him on the set of Don’t Worry Darling, which she directed
  • Following constant drama and headlines, Harry and Olivia reportedly split after nearly 2 years together in Nov. 2022

Olivia Wilde‘s past long-term relationship with Jason Sudeikis and her most recent romance with Harry Styles are two of the most talked about relationships in Hollywood. Between being served legal custody papers on stage in front of an audience and the love she found with the British singer while directing him for her film Don’t Worry Darling, there have been several public factors surrounding both of Olivia’s relationships that have had fans on their toes and rumors swirling. And, after nearly two years, she and Harry have also reportedly split as of Nov. 2022.

Most recently, a woman who was employed by Olivia, 38, and Jason, 47, as their children’s nanny shared several alleged details about the downfall of Olivia and Jason’s marriage to the Daily Mail. For example, she spoke about an explosive fight during which the Ted Lasso actor allegedly laid down in front of Olivia’s vehicle so she could not drive to set to see her now reported ex Harry, 28. She also claimed Jason signed her up for life coaching lessons in which she was given information about Olivia and was fired by a “drunk and out of control” Jason after he found out she was in contact with Olivia.

Although the relationship between Olivia and Jason has seemed completely sour as of late, they issued a joint statement on Oct. 17, 2022 and slammed their former nanny’s statements as fabricated. “Her now 18-month-long campaign of harassing us, as well as loved ones, close friends and colleagues, has reached its unfortunate apex,” they added. “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.“ Olivia and Jason share two kids: son Otis, 8, and daughter Daisy, 6.

Of course, the nanny’s allegations are just the tip of the iceberg regarding the drama revolving around Olivia’s love life. Read on to learn all there is to know about Harry and Jason’s involvement with Olivia.

Harry Styles And Olivia Wilde

Harry And Olivia Meet

Harry Styles and Olivia Wilde
Harry Styles and Olivia Wilde visit a pizzeria in Aug. 2022 (Photo: BeautifulSignatureIG / SplashNews)

Harry, who became a global superstar after being a founding member of the X Factor-formed band One Direction, was hired to star opposite Florence Pugh in the Olivia-directed Don’t Worry Darling after former child star and troubled actor Shia LaBeouf, 36, departed the film before production was underway. There’s drama there as well, as Olivia and Shia have voiced differing stories about Shia’s exit from the movie, and whether or not he stepped down or was fired remains unclear.

Regardless, Harry was hired and he and Olivia quickly hit it off on set. The movie began shooting during the fall of 2020, and just days after New Year’s Eve, the House actress was spotted holding hands with the “Golden” hitmaker at a wedding. That month, an insider revealed to HollywoodLife EXCLUSIVELY that Harry has no plans to publicly announce his relationship with Olivia. “He respects people he dates, and he knows it’s not just about him,” another insider explained. “There are two people involved, and out of respect, he just doesn’t discuss things that are just between them.” There is a bit of a gray line regarding when Olivia and Jason officially broke up and when Harry and Olivia got together.

The following month, a person close to Harry divulged to HollywoodLife EXCLUSIVELY that he “really likes Olivia, but he doesn’t want to make it a relationship that’s always in the news.” They added, “He wants their relationship to be between the two of them, and that’s why he doesn’t want to talk about it, because he doesn’t want Jason to feel bad or threatened by him.”

Did Harry And Olivia’s Romance Cause Problems On Set?

Although Harry and Olivia never confirmed their relationship, they were spotted throughout 2021 and 2022 holding hands and packing on the PDA, such as during a date night in London and a romantic yachting trip in Italy. However, all of their interaction vanished when it came time to promote Don’t Worry Darling with the rest of the cast. In fact, the duo was so distant, fans assumed they split up amid all the drama that simultaneously plagued the film and their relationship. However, amid the press tour, which seemed to have the whole world watching vigilantly, an insider told HollywoodLife EXCLUSIVELY that all is well between Olivia and Harry and that the duo was “trying to keep the focus on the movie.” They added, “They intentionally decided to keep the focus off their relationship by not walking the carpet together because they don’t want to distract any more from the movie.”

Don't Worry Darling cast
The cast of ‘Don’t Worry Darling’ poses on the red carpet, with Florence Pugh, Olivia Wilde, and Harry Styles separated (Photo: Anthony Harvey/Shutterstock)

The decision came as the rumors of a falling out between Olivia and Florence were the hot topic surrounding the film. In fact, it was reported that Florence was so disgusted by Harry and Florence’s relationship that she and Olivia got into a “screaming match” on set because Olivia would allegedly “disappear” with the “Watermelon Sugar” singer. However, Michael De Luca and Pam Abdy, CEOs and co-chairs at Warner Bros, denied the rumors of tension during production. “We are so proud of the work that Olivia Wilde has done making this incredibly beautiful and entertaining film and look forward to collaborating with her again,” a statement provided to HollywoodLife on their behalf read. “The studio is very grateful and appreciative of the tireless support by Olivia in bringing her vision to life from production through release.  Any suggestion of conflict between the studio and Olivia is simply not true.”

Are Olivia And Harry Still Dating?

Following constant drama and headlines around Don’t Worry Darling, the pair reportedly split after nearly 2 years together in Nov. 2022. The couple are “taking a break,” PEOPLE magazine reported, citing multiple sources. “He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A…It’s a very amicable decision,” the publication also said.

The split comes after rumors that the they had split, despite Olivia being spotted several times dancing the night away at Harry’s Madison Square Garden concert residency in New York City that took place in August and September, as he was also promoting his film. Furthermore, a source EXCLUSIVELY told HollywoodLife in the weeks ahead of the split that the two lovebirds are “stronger than ever” amid the storm of drama surrounding their relationship and film. “Despite rumors suggesting that there was trouble in their relationship, this entire experience has, in fact, made them stronger than ever,” the source explained. “They both really wanted to keep their relationship out of the spotlight when they were promoting this film and they think that they did this. The love that they share this unbreakable bond, and they are both so supportive of each other’s careers and would never do anything to let that come in the way of their relationship.”

Less than a month before the break-up, Harry had helped Olivia get her kids’ costumes for Halloween ready and was “totally invested” in it, according to another insider. “Harry gets along great with Olivia’s kids [and] they’re very fond of him. As mature as Harry is for his age, he’s also a kid at heart, especially when it comes to Halloween,” they noted to HL, EXCLUSIVELY.

Jason Sudeikis and Olivia Wilde

Jason And Olivia Fall In Love

Jason, who is known for his roles in Ted Lasso, We’re the Millers, and Horrible Bosses, and Olivia seemed like a dream couple at one point. They first met on the set of Saturday Night Live in May 2011. “I met Jason, and I thought he was so charming. He’s a great dancer and I’m a sucker for great dancers. But he didn’t even get my number,” Olivia recalled to Allure in 2013 (via People).

Olivia Wild Jason Sudiekis
Olivia Wild Jason Sudeikis pose at the Vanity Fair Oscars After Party (Photo: Evan Agostini/Invision/AP/Shutterstock)

The pair then started running into each other over the next six months, but did not start talking to each other until Olivia’s friend gave Jason her number. “[One night], my best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning,” Olivia added.

Jason revealed he did not reach out to Olivia for a few weeks because of bad information he received about her. “I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone,'” he remembered on The Late Show With Stephen Colbert in 2017. “So I didn’t make any 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.”

Jason and Olivia were finally able to meet up with intention, and the sparks flew. They began dating in the fall of 2011 and were engaged in Jan. 2013.

Jason And Olivia Start A Family

Olivia Wilde and Jason Sudeikis watch a basketball game with their kids in Feb. 2020
Olivia Wilde and Jason Sudeikis watch a basketball game with their kids in Feb. 2020 (Photo: John Photography/Shutterstock)

Jason and Olivia were in no rush to walk down the aisle. Rather, they had babies on their brains. “We’ve discussed all our ideals and hopes. I can’t wait for children. I’m open-minded about how many, but three, which I love, is like a little party,” the BoJack Horseman actress gushed to Marie Claire in March 2013. “I am not trying to have kids now — there’s no strict plan for anything in my life. What happens, happens. He’s so good with kids.” She sweetly added, “I’ve never before experienced looking at someone and thinking, That’s who I want to raise a child with.”

A few months later, the pair made something special together: a movie. The Virginia native ended up playing Olivia’s boss in Drinking Buddies after he simply visited Olivia on the movie’s set. “We roped him in,” she revealed to ABC News in 2013. “He didn’t know he was gonna have to work, he came to visit me in Chicago before he went to shoot We’re the Millers, and he came to lunch onset, and I was like, ‘Listen, we don’t have anyone to play my boss, will you just jump in and improvise with me for an hour?'” she recalled. “And he’s like, ‘Yeah, great, let’s go.'”

Just a month later, they announced they were expecting their first child together. As mentioned above, Olivia and Jason went on to have two kids together. The pair never got married, and Olivia reasoned that having kids was a more serious commitment than marriage in a 2014 chat with GLAMOUR. “In many ways, a child is more of a commitment. We are fully committed and really happy as a family,” she gushed. “And there’s no definition of the ‘normal family’ anymore. Kids today are growing up with so many different definitions of family. I guess what I’m saying is that I don’t feel any pressure to do it. But I think it will be really fun.”

The pair never had a third kid, but they adopted a dog together, named Maxamillion, in 2017.

Jason And Olivia’s Relationship Ends

After a few more years of non-marital bliss, Jason and Olivia’s relationship was reported to be on the rocks. In Nov. 2020, their split was official. “The split happened at the beginning of the year,” a source close to the former couple told PEOPLE. “It’s been amicable and they’ve transitioned into a great co-parenting routine.” The divorce seemed to be going amicably, and the pair were even spotted hugging in Nov. 2020 following the news of their divorce. Plus, Jason gave a sweet and subtle nod to his ex on the set of Ted Lasso, which was spotted by fans after he gave 60 Minutes a tour of the locker room set of the popular show.

Furthermore, Jason thanked Olivia while accepting his Critics Choice Award for Ted Lasso, which won best comedy series in 2021. “I want to thank [my kids’] mom Olivia, who had the initial idea to do this as a TV show, saying, ‘You and Brendan [Hunt] and Joe [Kelly] like doing that so much, you should do it as a movie or TV show,'” he said. She even responded via a joke about Jason’s casual attire for the virtual show on Twitter, writing, “So happy for you guys. I hope this means we all keep wearing hoodies when the ceremonies are in person next year.”

Then, in July 2021, Jason broke his silence on the divorce and hinted that he was confused by the separation. “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,” he told GQ“That’s an experience that you either learn from or make excuses about,” he continued. “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.”

Unfortunately, things took a turn for the worse during the latter half of 2021, and Jason had someone on his team serve custody papers to Olivia while she was on stage at a CinemaCon presentation in April 2022. The yellow envelope read “private and confidential” and an insider gave HollywoodLife more insight into what was in them. “[They were] papers were drawn up to establish jurisdiction relating to the children of Ms. Wilde and Mr. Sudeikis,” the source told HL EXCLUSIVELY.

Olivia Wilde cinemacon
Olivia Wilde speaks on stage at 2022 CinemaCon with the legal papers in her hand (Photo: Stewart Cook/Shutterstock)

They also said Jason did not know the papers would be served in such a public way. “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,” they explained.

A few months later in Aug. 2022, Olivia recalled the incident and claimed Jason tried to “sabotage” her. “I hated that this nastiness distracted from the work of so many different people and the studio that I was up there representing,” she reflected in Variety’s first-ever Venice Film Festival issue. “To try to sabotage that was really vicious. But I had a job to do; I’m not easily distracted.”

She added, “But, you know, sadly, it was not something that was entirely surprising to me. I mean, there’s a reason I left that relationship.”

Olivia Denies Cheating On Jason With Harry

Olivia put her foot down against rumors that she cheated on Jason with Harry during her Sept. 2022 cover story for Vanity Fair.  “The complete horses—t idea that I left Jason for Harry is completely inaccurate,” she stated. “Our relationship was over long before I met Harry. Like any relationship that ends, it didn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic. We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to NOT, because we could be better parents as friends who lived in different houses.”

Olivia Wilde, Jason Sudeikis
Olivia Wilde and Jason Sudeikis walk with their children at the Women’s March rally in Jan. 2018 in Los Angeles (Photo: Broadimage/Shutterstock)

Then, at the end of the month, she talked to Kelly Clarkson about the “tricky” co-parenting situation with her ex. “It’s tough. I think, you know, reshaping a family is tricky, and the one benefit is it’s allowed for some really deep conversations with my kids about emotions and about happiness and about what family means and love and it’s actually allowed me to get to know them in a different way,” she explained.

She added that she simply wants what is best for her children. “My priority is them. As long as they’re happy and they’re healthy then — my ex and I, we agree on that. They are everything to us. There are so many families that are blended and different shapes,” she said.