Olivia Wilde Shares Rare Insight Into “Loveliest” Harry Styles Romance

by

Olivia Wilde is looking back on her time with ex Harry Styles as it was.

More than three years after their split, the director of Don’t Worry Darling revealed details about her relationship with the former One Direction member, saying people were very angry when they first began dating.

Olivia discussed the public reaction to her relationship with Harry during a recent podcast episode. She said the age difference – Harry was 26 and she was ten years older when they began dating – really bothered some people. “It was crazy,” she explained, adding that she’s still processing it all and acknowledging there was significant public outrage.

Olivia, who has two children – Otis and Daisy – with her former partner Jason Sudeikis, also suggested that the public’s reaction might be because people feel a one-sided connection to her and the singer.

She described their relationship as wonderful and surprisingly cozy. She said it was incredibly sweet, beautiful, and felt very much like a loving home life.

She explained that they had created a protective environment for themselves, and somehow managed to shield it from outside criticism – which she felt was remarkable and a credit to their efforts.

Olivia Wilde has rarely spoken about her relationship with Harry Styles, but recently opened up after they began dating several months after he joined the cast of her film, Don’t Worry Darling, in late 2020. Just before filming finished in early 2021, Olivia – who had officially ended her relationship with Jason Sudeikis earlier that year – told Vogue magazine about the decision to cast Styles in the now-famous movie.

Olivia Wilde recalled being thrilled when Harry Styles joined the film, explaining that costume designer Arianne Phillips and she celebrated because they knew he genuinely cared about fashion. She appreciated his enthusiasm for style, noting that not all actors share that interest.

When Harry posed in a dress for a photoshoot with Vogue magazine, Olivia was quick to publicly support him.

She told Vogue she finds him very forward-thinking, and hopes his self-assuredness—which isn’t tied to harmful ideas about masculinity—represents a positive shift in his generation and for the future. She believes he’s leading the way in redefining what it means to be a confident man, and that’s really impactful and inspiring.

Harry and Olivia generally kept their relationship private before they broke up in 2022, but Olivia admitted she often wanted to clarify inaccurate stories about them being together.

In a 2021 interview with Vogue, she explained that true happiness comes from focusing on what genuinely matters – your loved ones and the things you cherish – and not worrying about the opinions of others.

Want to see more celebrity couples who stayed friends even after breaking up? Keep scrolling to find out…

They are definitely not getting back together. However, with all the recent interactions – birthday celebrations, affectionate hugs, and even a playful recreation of a romantic scene during the Fast Times at Ridgemont High virtual reading – it feels like they’re just teasing everyone who hoped they’d reconcile.

Sarah proved she’s confident and playful when she appeared on her ex-husband Jimmy’s talk show. She was there to promote her new series, I Love You, America, and playfully teased Jimmy about his wife, Molly Kimmel, describing her as “cute,” “bright,” and “funny.” Jokingly, Sarah complained, “It’s not fair! She gets the updated, more aware Jimmy. I only had the Man Show Jimmy.”

 

Honestly, some people seemed more upset about this breakup than those who were actually in the relationship. When Anna—who is now married to Michael Barrett—found out Chris Pratt was going to marry Katherine Schwarzenegger in 2019, she volunteered to perform the wedding ceremony. She even sent a gift when their daughter Lyla was born in August 2020. A source reported that Anna was happy for her son Jack to have a little sister and that she was very supportive of the new family.

Their breakup could have easily led to disaster, but four years later, these HGTV stars are thriving. They’re successfully co-parenting their children, Taylor and Brayden, and continuing to renovate dilapidated houses into beautiful homes for others.

Lenny Kravitz described his relationship with Lisa Bonet – the mother of actress Zoe Kravitz – as a close, familial bond during a 2013 interview with Oprah Winfrey. Despite their divorce, they still feel like family. “We’re one big happy family,” Lenny explained, adding that it’s wonderful to see how well they all get along, even after Lisa married and later split from Jason Momoa in 2020. He believes it demonstrates what’s possible when people prioritize positive relationships.

Since announcing their split in 2020, the Dancing With the Stars co-host and her former hockey player husband have consistently shown they remain friendly with each other.

When Brooks announced he was getting engaged to Katrín Tanja Davíðsdóttir in December 2024, Julianne publicly shared her excitement on Instagram. She wrote that she was thrilled for the couple as they started this new phase of their lives and wished them a future filled with love, joy, and many adventures.

Several months after their split, the dancer reunited with her ex-husband and his pregnant fiancée for a day at the lake. She shared a photo of the four of them, calling them “three cuties” in the caption.

After separating in 2015, the parents of Violet, Seraphina, and Samuel have successfully co-parented, managing to take family vacations together, celebrate holidays as a unit, and publicly support each other. In a 2016 interview with TopMob News, Ben praised his former partner as “an amazing mother.”

Nina and Ian broke up in 2013 after dating for three years, but they stayed friends. The following year, Nina began a relationship with Nikki Reed and quickly married her. As a result, Nina became friends with the Twilight star.

The couple ended their five-year relationship in July 2016. The singer later shared on The Howard Stern Show in October that she remained very close to her ex, stating he had been both a lover and a friend for a long time.

“We love each other,” she said. “That’s it.”

Even years after The Office ended in 2013, the chemistry between its stars remained obvious, and Mindy Kaling understands why fans still hope they’d get together. In a 2019 interview with Good Housekeeping, she admitted that if she were a viewer, she’d feel the same way. However, she explained that B.J. Novak is now more like family than just a friend, which is why she chose him to be a godparent to her children.

Okay, so Pete Wentz and Ashlee Simpson finalized their divorce way back in 2011, but honestly? They’re amazing at co-parenting little Bronx! I read that Pete actually said Ashlee is a seriously awesome mom, and it just melts my heart. It’s so good to see them putting their son first, even after everything. Seriously, they’re #ParentingGoals!

It sounds like she’s moved on from her past relationship with the singer. He’s stated they are still on good terms and remain friendly, describing their connection as a positive one.

Jennifer and her Dexter co-star first connected on the show’s set in 2006, and their relationship became romantic two years later. Even after divorcing in 2011, Jennifer has said they remained friendly and supportive of each other.

As someone who’s seen it all when it comes to blended families, Bruce Willis and Demi Moore truly set the bar! They’ve always had an incredibly supportive relationship as parents to their daughters – Rumer, Tallulah, and Scout. So, when stay-at-home orders hit with the pandemic, honestly, it wasn’t a surprise they decided to quarantine together in Idaho. It just felt natural for them to support each other and their girls. I heard there was even a dance party or two! It’s wonderful to see such positive co-parenting in action.

Even four years after their divorce in 2014, Jennifer Lopez continued to praise her ex-husband and the father of her twins, Max and Emme. In a 2018 interview on Sunday Today, she shared how Marc Anthony boosted her confidence during their marriage. He encouraged her, saying she was a talented singer and shouldn’t let anyone diminish that. She deeply respected him, considering him one of the greatest singers ever.

Despite any personal struggles he might be facing, the actress will always support her ex-husband and former Scream colleague. She described their divorce – which happened in 2010 – as surprisingly amicable, saying on Running Wild With Bear Grylls eight years later, “It’s definitely been one of the smoother divorces.” They’ve successfully co-parented their daughter, Coco, and maintain a good relationship.

Although their relationship ended in 2007, they still had great chemistry on screen when they starred together in the 2011 film Bad Teacher.

Although their 2013 breakup was difficult at first, the actors have reached a point where they can vacation together as a group. The actor shared with LaPalme Magazine that he gets along well with his ex-wife’s husband, describing him as a “great guy.” He mentioned a 2017 trip to Cancun where they were joined by her husband, Dave Abrams, Peter’s fiancée Lily Anne Harrison, and their three daughters: Luca, Lola, and Fiona. He also reflected on his relationship with his ex-wife, telling the magazine that people enter our lives for a reason and relationships evolve, adding that love can still exist even when a couple isn’t together.

I’ve always admired how Will and Jada handled things, even when they privately separated back in 2012. They really prioritized their kids, and put on a brave face for them. I remember Jada talking to Howard Stern in 2014, and she explained they were still incredibly close friends and doing a great job co-parenting. She even said she didn’t view their ten-year marriage as a failure, which I thought was a really mature and insightful way to look at things. Relationships are hard, and they proved you can navigate those challenges with grace.

The Grammy-winning artist and her ex-husband, who officially divorced in January 2024, have maintained a friendly relationship while raising their son, Hayes. They even live only five minutes away from each other, making it easy to share parenting responsibilities.

“Our stops are really easy,” Maren told The Zoe Report in May 2025, “and we’ll have family dinners.”

Read More

2026-06-17 15:49