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Olivia Wilde Is ‘Trying Not to Be Jealous’ of Harry Styles & Emily Ratajkowksi Making Out—It ‘Upsets’ Her

Even John Legend had something to say about their makeout.
Olivia Wilde, Harry Styles, EMily Ratajkowski
Image: Getty Images

Moving on too quickly? The Harry Styles and Em Rata kissing video has been plastered in our minds. The real question is: How does Olivia Wilde feel about Harry Styles and Emily Ratajkowski dating?

On March 25, 2023, the Daily Mail published a video of the “Watermelon Sugar” singer and the model kissing after one of his Love on Tour shows in Tokyo, Japan. The video immediately went viral and had some sharp reactions online. Even John Legend had to react to it, “Making out to Dope. So dope” he referenced the song that he made with JID which was playing out in the background of the makeout video.

So how did Harry’s ex-girlfriend Olivia Wilde react to the news? Read more below to find out.

How did Olivia Wilde respond to Harry Styles dating Emily Ratajkowski?

Emily Ratajkowski, Olivia Wilde
Image: Kevin Mazur/VF23/WireImage for Vanity Fair

How did Olivia Wilde respond to Harry Styles dating Emily Ratajkowski? According to a source to Page Six, it’s not going too well. The source told the gossip site that Olivia thinks that “This is a betrayal.” Meanwhile, the Gone Girl actress is “begging her for forgiveness.”

“She is staying far away from this and taking the high road,” the source told the site of the Don’t Worry Darling director. “She is focused on her kids and her work. She wants nothing to do with this mess.” Another source told Us Weekly that Olivia “is trying not to be jealous because she is moving on as well.” The source also said that the makeout video “upsets” Wilde.

When news broke of the new fling. after the Tokyo kiss, a source told People that “Harry and Emily know each other,” noting, “They have been friendly for a while.” The insider also noted that she was also friendly with Wilde. In a resurfaced video from 2015, Harry called the model his “celebrity crush”.Another source told Us Weekly “Harry has always been very attracted to Emily,” and is “thrilled” about “hooking up” with her. Sources also told the site, “Everyone is happy because they’re both single and really enjoying their carefree romance,” the insider said, noting that “friends don’t know” what lies ahead for their relationship.

Harry and Olivia broke up in October 2022 after being together for more than two years. One source People that Harry’s Love On Tour affected the status of their relationship. “He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A.,” a source said. “It’s a very amicable decision.” The Don’t Worry Darling star and director are still “very very close friends.” However, their careers and family life are in two distinct places.  “Right now, they have different priorities that are keeping them apart,” another source dished.

According to an insider quoted in Us Weekly, Olivia was “still very much upset about the breakup” and that she was trying to “move on” by taking a girl’s trip. “Olivia thought going on vacation would allow her to decompress,” the insider said. This sentiment was backed up by a source quoted by People, who said: “The break has been difficult for Olivia. They have had some issues, but Olivia thought they were gonna work through it all. She is disappointed. It’s just a tricky situation, though.”

Since the news broke, people close to Olivia and Harry have been providing reasons for their relationship breakdown. “The public pressure on them has been difficult,” a friend of the ex-couple told People. “They’ve had ups and downs throughout the relationship.” The main tabloid allegation that revolved around the ex-couple was that Olivia cheated on her then-fiance Jason Sudeikis with Harry while filming her second directorial project. The two started dating on the set of their movie Don’t Worry Darling where Olivia directed and Harry starred. At the time, Olivia was still engaged. Olivia and the Ted Lasso star were together from 2011 until November 2020. The couple got engaged in 2013 and share two children together: Otis, 8, and Daisy, 5.

Olivia talked about how the ongoing rumors of her relationship affected her in a Vogue profile. “It’s obviously really tempting to correct a false narrative,” she said. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about it. All that matters to you is what’s real, and what you love, and who you love.”

Harry Styles, Olivia Wilde
Image: Neil Mockford/GC Images

Meanwhile, Em Rata had just recently divorced her husband of 4 years Sebastian Bear-McClard. She filed for divorce in Manhattan Supreme Court Thursday and noted it was contested, meaning there are issues to be litigated. Page Six first reported the divorce on September 9, 2022 and news of the split was first reported in July 2022. Sources close to the couple reported to the outlet that the split was due to Bear-McClard’s infidelity. “Yeah, he cheated,” the insider told Page Six. “He’s a serial cheater. It’s gross. He’s a dog.” A week after the news of her divorce, Ratajkowski was photographed in New York City in a baseball cap with the French quote: “Ce n’est importe quoi,” which loosely translates to “It doesn’t bother me” in English.

The model has since been casual dating and grabbed the attention of Brad Pitt, Pete Davidson, Eric Andre and more. She talked about how the paparazzi had “screwed up” dating for her. “I’ve gone on dates where there’s been no pictures, and I’m like, ‘All good’, ” she said. “And then there’s been times where literally the first time that I’ve met someone, we spent 2 hours together, and there’s pictures on the Internet.”

Em Rata defended her friendship with Olivia “In the past year with Amber Heard and Olivia Wilde and the craziness of putting them in this box as if they’re monsters or witches. . .There’s nuance to it, but when you see the way that the whole world reacts to women, it’s really hard not to want to go to an extreme side of it,” Ratajkowsk told Elle UK. “I feel very protective.”

“I really wanted to be chosen,” the model shared with the magazine. “It was hard for me to go on a date with someone and think about how much I did or didn’t like them. I would have been thinking about how they were perceiving me, what it meant, what they wanted from me, what it meant about my self-worth. I don’t have that anymore,” she said. “So now it’s really fun to go to dinner with someone and be like, ‘Cool. I really enjoyed these parts of them. I really didn’t like these other parts.’”

"My Body" by Emily Ratajkowski
Image: Courtesy of Metropolitan Books.

My Body by Emily Ratajkowski

My Body is a profoundly personal exploration of feminism, sexuality, and power, of men’s treatment of women and women’s rationalizations for accepting that treatment. These essays chronicle moments from Ratajkowski’s life while investigating the culture’s fetishization of girls and female beauty, its obsession with and contempt for women’s sexuality, the perverse dynamics of the fashion and film industries, and the gray area between consent and abuse.

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