Harry Styles Regrets Ending Things With Olivia Wilde As She Starts Fresh With Actor Dane DiLiegro

Harry Styles is wistful about his two-year romance with Olivia Wilde. “He has regrets about how everything turned out,” notes a source.

The 31-year-old split from Taylor Russell last May, and the source says that a year of singlehood has made the former One Directioner reflect on his romance with his Don’t Worry Darling director, 41.

“There’s something different about Olivia compared with anyone else he’s been with,” adds the source. “He knows now that you don’t find that kind of chemistry every day.”

Gregg DeGuire / Image Press Agency / MEGA

Meanwhile, Olivia has moved on, reportedly dating actor Dane DiLiegro since January.

“She was crushed when Harry ended things in 2022,” says the source, who suggests Harry’s touring schedule wasn’t compatible with Olivia’s life as a mom to her kids with ex Jason Sudeikis. “As time went on she concluded she needed a more mature, stable partner.”

How Harry Styles Allegedly Feels About Olivia Wilde Moving On With Her New Beau Years After Feeling ‘Gutted’ About Their Own Breakup

Throughout the years, plenty of celebrity relationships have managed to capture the public’s attention. Olivia Wilde and Harry Styles made headlines in a big way back in 2021 when it was reported that they were dating. What followed was a cavalcade of media coverage that also encompassed the film the two collaborated on, Don’t Worry Darling. They ultimately broke up in late 2022, and Wilde is currently dating Dane DiLiegro. Now, an insider is dropping claims on how Styles feels about his old flame’s new romance.

It’s somewhat hard to believe it’s been a few years since Harry Styles and Olivia Wilde split up. The two never provided specific details about the circumstances surrounding their split. Now, an insider tells OK Magazine that the now-31-year-old ex-One Direction member was actually “gutted” when his romance with the Rush star came to a close. Nevertheless, Styles supposedly holds no hard feelings towards Wilde as she embarks on her latest relationship:

He still cares about her and wants to see her happy.

Before linking up with the “As It Was” singer, Olivia Wilde was in a long-term relationship with fellow actor Jason Sudeikis. The pair were together from 2011 to 2020, and they share two children, Otis (10) and Daisy (8). When Sudeikis and Wilde split, there were reports of drama between the two, which seemingly came to a head when the Ted Lasso star apparently served his ex while she was presenting at CinemaCon in 2022. Ahead of that, rumors ran around in regard to the timing of Wilde’s breakup with Sudeikis and the start of her relationship with the aforementioned pop star.

Considering that Harry Styles was purportedly in his feelings over his split from the Tron: Legacy star, some may be tempted to assume he was the dumpee. The same source suggested to OK, however, that the Grammy winner was the person who initiated the breakup, and they dropped claims about why Styles supposedly felt bad about doing that:

It’s just a massive relief to see that she’s finally met someone new. Harry was gutted when he realized he wanted out of his relationship with Olivia, because he knew she would take it hard, and in fairness, he had made a ton of promises to her. He always feels bad when he has to break a girl’s heart, but with Olivia he felt a hundred times worse because she’d put so much on the line for him, he felt so [bad] letting her down. And then it took so long for her to let go, she was wearing his shirts in public for ages after they split up, it was rough.

While both Olivia Wilde and Harry Styles rarely spoke about their romance publicly, there were instances in which they shared candid thoughts on the public’s reaction to it. Wilde acknowledged that a “false narrative” regarding her relationship was spreading around, though she said she wouldn’t engage with that chatter. For his part, Styles got real about the “toxic negativity” that surrounded him and his partner, admitting that it was hard on him.

This latest report regarding Harry Styles should be taken with a grain of salt, though his alleged thoughts on Olivia Wilde would track. On the rare occasion he’s discussed her, he’s only shared positive thoughts, and he praised Wilde as a director as well. We can only speculate as to where these former lovers truly stand but, ultimately, one would just hope they can continue to move on in ways that best suit them.