The newest and most exciting Hollywood couple to pay attention to right now is Olivia Wilde and Harry Styles. The details of their newfound romance are too interesting to ignore! Especially when some of his famous ex-girlfriends are supermodel Kendall Jenner and singer/songwriter Taylor Swift. Is Olivia Wilde the woman that is finally going to steal his heart for good?
Pictures of the two holding hands surfaced online in early January 2021, and social media has collectively reacted. Some fans were downright shocked and others were immediately happy for the two. Others are questioning the timeline of their romance and wondering if there has been any overlap in regards to her past relationship with Jason Sudeikis.
10 Olivia & Jason Sudeikis Split Up At The Beginning of 2020
Olivia Wilde and Jason Sudeikis weren't just dating, they were engaged! They decided to call it quits at the start of 2020 but the public did not find out about the news until several months after the fact. People Magazine reported that the breakup was amicable. No hard feelings, no bad blood. It's important to note that the public wasn't in the loop about their split just yet.
9 Harry Was Cast In Olivia's Movie 'Don’t Worry Darling' In Place Of Shia LaBeouf, October 2020
In September of 2020, Deadline reported that Harry was cast alongside Olivia Wilde in her newest movie, Don’t Worry Darling. Olivia isn't going to be acting in the movie, she is actually going to be directing it. After an apparent fallout between herself and Shia LaBeouf, she re-casted the role with Harry Styles who will be acting opposite Florence Pugh from Midsommar.
8 Olivia Spoke Highly Of Harry Styles's Fashion Sense In November 2020
In November of 2020, Olivia Wilde made it clear to just about everyone how excited she was to be working with Harry Styles. According to Vogue, Olivia Wilde said, "... 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. 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.” His fashion choices for his Vogue photoshoot have opened up the dialogue to a lot of conversations about fashion, style, and modern-day trends for the male gender.
7 Olivia Complimented Harry's Confidence Also, November 2020
According to The List, Olivia Wilde is impressed by Harry Style for a multitude of reasons. She said, "To me, [Harry'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."
She 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.” She clearly had such a high level of respect for Harry as well as the way he expresses himself and carries himself.
6 The Public Found Out About Olivia & Jason Sudeikis's Broken Engagement In November 2020
It wasn't long after reports of Olivia Wilde's admiring words for Harry Styles were published that the world found out about her split from Jason Sudeikis. Although they'd broken up months prior, no one really knew until November of 2020. Since the ex-couple share two children together, they were already handling the co-parenting deal like plenty of other ex-couples.
5 Olivia & Harry Were Photographed Holding Hands, January 2021
In January of 2020, Harry and Olivia were spotted holding hands! The pictures were captured at a wedding located in Montecito, California. Everyone on social media had something to say about the new potential couple.
Holding hands is one thing. Holding hands at a WEDDING is another thing. Holding hands at a wedding where paparazzi cameras can catch you is on a whole other level. They were cool with the world finding out.
4 A Source Claimed That Harry & Olivia Grew Close On The Set Of 'Don’t Worry Darling'
According to Entertainment Tonight, a source explained how the relationship between Olivia Wilde and Harry Styles came to be. The source said, "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.” Working in close contact with another person can lead to new feelings developing so this obviously makes sense.
3 Stories Blaming Harry For Causing The End Of Olivia & Jason Engagement Started Up
In January 2021, a source told Us Weekly a source said, “Olivia called off the engagement in early November but only after she already had gotten close to Harry. Whether Harry knows it or not, he was a reason for the split and it blindsided Jason—he totally adores Olivia and is devastated. Family is his biggest priority.” Yikes! Whoever said that seemed convinced that Harry caused the demise of an otherwise healthy engagement.
2 A Source Confirmed That Harry Did NOT Break Up Olivia's Engagement
A different source also spoke to Us Weekly about the situation in January. This one said that Harry most certainly did not break up the engagement between Olivia Wilde and Jason Sudeikis. The source clearly said, "Harry did not break up an engagement.” This source made it clear that Harry entered the picture way after Olivia was already a single woman.
1 Jason Sudeikis Apparently Wants To Win Olivia Back
According to Elle Magazine, Jason Sudeikis wants to patch things up with Olivia Wilde if it's possible. A source said, “Jason’s had no option but to step back and let Olivia do her thing, but he [has his fingers crossed] that this is just a phase and that Olivia will snap out of it or that Harry will get bored and move on before too long. He’s desperate to win Olivia back to repair their family.” Jason Sudeikis himself has not made a statement about yearning for reconciliation but fans are reportedly mocking him over his alleged sentiments.