'Surprised' Olivia Wilde Reportedly Feels Ex Harry Styles' Romance With Pal Zoë Kravitz Is 'Super Awkward'

Harry Styles' budding romance with Zoë Kravitz may have shocked many, but perhaps none more than his ex, Olivia Wilde, who reportedly feels a certain way about it.

Wilde and Styles were romantically involved from early 2021 until November 2022, after they connected on the set of her film "Don't Worry Darling."

However, just last month, the former One Direction singer and the "Big Little Lies" alum sparked relationship rumors after they were spotted walking arm in arm in Rome. They have also made other public appearances, including Styles meeting Kravitz's dad. 

Though it's been three years since Wilde and Styles split and both have moved on, his new affair still seems to affect Wilde, according to the Daily Mail.

"Olivia is surprised Harry is dating Zoe," an insider told the outlet. "It always feels weird to her when Harry starts dating a new celebrity." 

The situation is even more tricky since Kravitz is Wilde's close friend, making it uncomfortable for her. "'It's like, why her? Why does he have to date people she knows? It's super awkward for her," added the informant.

However, another source revealed a different view, claiming Wilde is unfazed by who the "Watermelon Sugar" singer dates, as their entanglement is long behind her.

"'Olivia thought that pairing was interesting, but she doesn't really give a crap because she and Harry dated so long ago," the individual disclosed. 

Aside from Kravitz, the "As it was" hitmaker has also been with another of Wilde's besties, Emily Ratajkowski. Styles and the supermodel made headlines in March 2023 when they were spotted kissing in Tokyo, marking the start of their short-lived fling. 

Other women that Styles has been linked to include his co-star Florence Pugh, along with Taylor Swift and Kendall Jenner. However, he was said to have been most serious with Wilde, who was even rumored to have inspired one of his hit songs.

For now, the British singer is with Kravitz, who appears to have settled on him despite recently spending time with Austin Butler.

Before "The Studio" actress was seen with Styles, she had been hanging out with Butler, her co-star in the new film "Caught Stealing." 

As The Blast reported, the pair were filmed drinking, hugging, and getting cozy at a bar following the film's launch. Although their closeness sparked speculation, a friend clarified that nothing romantic is happening between Butler and Kravitz. 

Just days after her outing with Butler, the "Fantastic Beasts" actress was seen with Styles, with a tipster claiming she's more drawn to him and that their connection is strong.

 "Zoe is attracted to musicians, but she is also attracted to Harry because he is really cool. He's really cool without trying." The source added that part of Zoë's attraction to the "Fine Line" singer is that he reminds her of her father, Lenny Kravitz.

Proving that their relationship is not surface-level, the "Blink Twice" star has even let her boyfriend meet her legendary dad. 

As The Blast documented,  three days earlier, Styles, Zöe, and Lenny were caught on camera walking into a restaurant. 

Zoë looked chic in her signature effortless style, wearing a slip skirt and flats, while Styles opted for tailored trousers and a crisp white shirt.

Lenny embodied his rock star image in a sheer vest that highlighted his toned frame, finishing the look with flared jeans and a bag. The dinner outing was undoubtedly a big step forward for the couple. 

As the "Sign of The Times" singer continues to flaunt his girlfriend, Wilde isn't keeping her own affair under wraps either. Just two days ago, she enjoyed a three-hour dinner with her rumored partner, Caspar Jopling, Ellie Goulding's ex-husband.

In pictures obtained by Page Six, the 41-year-old actress was photographed kissing the 33-year-old art dealer outside London's The Pelican restaurant. 

According to onlookers, the pair were very much all over each other and "seemed very comfortable and relaxed in each other's company."