As a big fan of Olivia Wilde, I have to admit I was a little worried when I saw photos of her at the San Francisco International Film Festival this week. People online seemed concerned, and honestly, so was I!
People are talking about Florence Pugh not only because a recent video showed her looking noticeably thinner, but also because of rumors that her ex-boyfriend, Harry Styles, is engaged to Zoe Kravitz after dating for just eight months.
When 37-year-old Florence Pugh was seen wearing a diamond ring worth around $1 million, attention quickly turned to Olivia Wilde, 42. Wilde’s two-year relationship with Harry Styles had previously been heavily publicized, including a lot of media attention and even jokes about a specific salad dressing recipe.
Despite splitting up almost four years ago, Olivia Wilde appeared positive while promoting her new movie, Don’t Worry Darling, at a film festival on April 24th.
According to a source speaking with the Daily Mail, Olivia Wilde is still affected by the emotional pain of her split with Harry Styles. However, the source also says both Wilde and Styles have moved on and are now happy with their lives.
According to a source who spoke with the Daily Mail, Harry found his split with Olivia to be particularly difficult, marking the most painful breakup he’d experienced.
He wrote a whole album detailing his personal experiences, but ultimately decided not to release it. He felt it was best to keep those songs private and focus on the future, according to a source.
‘Now that he’s met Zoe, he is so happy and it all makes sense why he went through that.’
Sources say Olivia was also deeply hurt by the split with Harry, but she’s since been seeing other people and is doing better now.
This week, a video from the San Francisco International Film Festival caused concern when it showed director Emerald Fennell looking very thin and seemingly unwell.
Following recent admissions of celebrities using weight loss drugs, some critics have spoken out against Hollywood’s pressure to conform to certain beauty ideals.
However, defenders suggested the distorted look was actually due to the camera angle of the video.
I was really surprised by all the talk about Wilde’s recent outing, but a source told the Daily Mail she actually gets quite upset by all the guessing and rumors. She doesn’t appreciate people speculating about her personal life, and honestly, I can’t blame her!
Olivia struggles with self-doubt, like many people, and worries about what others think of her. Being famous doesn’t change that; she’s still human.
Rumors about a possible engagement between Harry Styles and Zoë Kravitz have resurfaced after Page Six reported they are engaged and that Styles is deeply in love with her. This news comes after nearly two years of dating.
Olivia Wilde and Harry Styles first connected on the set of her movie, Don’t Worry Darling, in late 2020.
In November, news broke that Olivia Wilde and Jason Sudeikis, 50, had called off their nine-year engagement.
The former couple share son Otis Alexander, 12, and daughter Daisy Josephine, nine.
Rumors of a romance between Wilde and Styles began in January 2021 when they were spotted holding hands at a wedding in Montecito, California – the wedding of Styles’ manager, Jeffrey Azoff.
The public sighting sparked a lot of reaction from Harry Styles’ fans, with many commenting on the age difference between him and Wilde. It also led to speculation and rumors that Wilde had been unfaithful to her then-partner, Jason Sudeikis, during the production of their film, Don’t Worry Darling.
The actress later shut down the cheating allegations in an interview with Vanity Fair.
She told the magazine in September 2022 that the rumor she left Jason for Harry is completely false. She explained that her relationship with Jason had ended well before she met Harry on set.
Breakups are rarely sudden, and Jason and I definitely had our struggles. We officially split up around the start of the pandemic.
But that didn’t stop the increased speculation into their relationship.
Rumors of a relationship between Olivia Wilde and Harry Styles started gaining traction in 2021 and continued into 2022. Reports surfaced in February 2021 that Wilde had moved into Styles’ Los Angeles home, with photos showing her bringing items in on Valentine’s Day.
That summer, they were photographed enjoying a romantic vacation in Italy, even sharing a kiss on a yacht in Monte Argentario. In September, Wilde was seen cheering on Styles at one of his Love on Tour concerts in Las Vegas, and later, she was spotted wearing a tour t-shirt a couple of months after that.
In December 2021, reports surfaced that Styles was gradually building a relationship with Wilde’s children. The following August, he told Rolling Stone he was starting to consider having children himself.
Though they generally kept their relationship details to themselves, many fans believed Harry Styles’ April 2022 song, “As It Was,” was inspired by the actress. The song includes lines like, “I don’t wanna talk about the way that it was, leave America, two kids follow her, I don’t wanna talk about who’s doin’ it first,” which fueled the speculation.
I really admire how Harry handles things with his personal life. He recently shared with Rolling Stone that he’s made a conscious choice not to get caught up in trying to control how the media portrays his relationships. He feels there will always be some kind of story out there, and he’s decided it’s just not worth his energy to constantly correct or steer the narrative. It’s a really healthy approach, honestly, and I think it protects the people he cares about.
Meanwhile, Wilde echoed their desire to protect their relationship in an interview with Variety.
She explained in August 2022 that she wouldn’t discuss the matter, believing relationships are better off kept private. She and her partner actively work to protect their connection, drawing on both past experiences and a strong foundation of love.
Oh my gosh, ‘Don’t Worry Darling’ finally came out in September 2022, and honestly, I was SO excited! But it was so frustrating because all anyone talked about wasn’t the movie itself, but all the stuff happening behind the scenes. It totally stole the spotlight from what I was really interested in – the film!
In April 2022, while presenting her film at CinemaCon in Las Vegas, Olivia Wilde received a sealed envelope labeled ‘Personal and Confidential’ from someone in the audience.
Sudeikis served Wilde with legal documents about their two children, delivered in an envelope. Wilde told Vanity Fair she was both saddened and upset by this method of delivery.
A spokesperson for Jason Sudeikis stated that he didn’t know his ex-wife would be served with custody papers in public, and he absolutely would not have approved of such a disrespectful method of service.
The breakup between the couple gained even more attention when their former nanny gave an exclusive interview to the Daily Mail, revealing personal details about the split. The nanny described Jason Sudeikis as devastated and claimed Olivia Wilde had become infatuated with Harry Styles.
She also stated that Sudeikis was extremely angry when he saw Wilde making a salad for Styles with her personal dressing in their kitchen. He reportedly yelled at her, and then attempted to stop her from leaving by lying down under her car.
Wilde and Sudeikis released a statement to the Daily Mail expressing their disappointment and upset that their former nanny had publicly made what they called false and damaging accusations about them as parents.
After 18 months of ongoing harassment towards us, our family, friends, and coworkers, the situation has unfortunately reached its worst point.
We’ll keep prioritizing our children’s well-being and safety, and we hope she will respect our family’s privacy and leave us alone now.
In February 2023, the couple’s former nanny sued them, claiming she was caught in the middle of their breakup and unfairly fired.
In August that year, a judge ruled for the case to be moved to arbitration.
A spokesperson for Jason Sudeikis and Olivia Wilde confirmed to the Daily Mail that the legal case had been completely resolved.
Olivia and Jason expressed hope that they can move forward after what they described as a greedy and public betrayal of their trust, motivated by money.
According to court documents published by the Daily Mail, the former couple reached a final agreement in their custody dispute in September 2023. The actor, known for Ted Lasso, will pay $27,500 each month in child support for their two children.
As a longtime follower of these two, I’m happy to share that they’ve worked out a really sensible arrangement for their kids, Otis and Daisy. They’re going to share custody, switching off weekly – one week with Mom, the next with Dad. It seems like a good way for the kids to have consistent time with both parents.
While Wilde was publicly fighting for custody, her romance with Styles seemed to fade.
News surfaced in November 2022 that Harry Styles and Olivia Wilde were separating temporarily. This coincided with Styles continuing his world tour while Wilde stayed in Los Angeles.
After a brief pause in their relationship, Harry Styles and Olivia Wilde ultimately broke up, with news surfacing in June 2023 that Styles was dating actress Taylor Russell.
Recently, Harry Styles has been linked romantically to model Emily Ratajkowski, singer Olivia Dean, and producer Ella Kenny, fueling speculation about his love life.
Rumors began circulating by August 2025 that he was dating Kravitz, as they were often seen together in photos taken across Europe and New York City.
It appears Olivia Wilde and Jason Sudeikis have developed a much more cooperative co-parenting relationship recently.
Shortly after reports began circulating about a possible engagement for Harry Styles, Olivia Wilde was spotted spending time with her ex-fiancé, Jason Sudeikis, in Los Angeles. She brought her children to his home, and the two shared a friendly embrace.
Following her breakup with Harry Styles two years ago, director Olivia Wilde was rumored to be dating basketball player Dane DiLiegro. Now, reports suggest she is seeing British art dealer Caspar Jopling, with their connection first appearing in September 2025.
Representatives for Wilde declined to comment to the Daily Mail.
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2026-05-01 01:21