Harry Styles can’t be happier for ex-girlfriend Olivia Wilde now that she’s finally moved on from their doomed romance with handsome athlete-turned actor Dane DiLiegro and a source exclusively tells Life & Style he was being torn apart by guilt over how heartbroken she was when he made the painful choice to end their relationship.
The One Direction alum, 31, and the House actress, 41, first got to know each other after Harry replaced Shia LeBeouf in Olivia’s movie Don’t Worry, Darling. They dated for nearly two years, surprising many fans who considered their fling pretty unusual at first. Though, according to the source, as their connection grew, the two were seriously considering spending the rest of their lives together, despite Harry ultimately pulling the plug. Their feelings for each other were strong enough to cause some serious pain as they went up in flames.
“Harry was gutted when he realized he wanted out of his relationship with Olivia, because he knew she would take it hard,” the insider says, “and in fairness, he had made a ton of promises to her.”
The Tron: Legacy star was with Jason Sudeikis for seven years and had two kids with the Ted Lasso star: son Otis, 10, and daughter Daisy Josephine, 8. The couple was even engaged at one point, but Olivia pulled the plug once she started getting cozy with the pop star.
“She had called off her engagement for him and put her career on the line, so clearly, she believed he was in it for the long run, too. And at first, he was even talking about marrying her,” the source explains.
The insider adds that, while Olivia was all in and head over heels, as evidenced by how firmly she devoted herself to the relationship, it was ultimately the British boy bander who lacked the courage of his commitment.
“The issue with him is he’s always all in at the start, but long-term commitment just never seems to work for him, even if he thinks that’s what he wants at the outset.”
“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 crap letting her down,” the source says. “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.”
Despite the heartbreak, the Booksmart director has been enjoying her time with her new beau, Dane, 36, a former pro basketball player turned actor. The Massachusetts native, who is 6-foot-8, has been mostly cast as horror movie monsters throughout his career so far — playing an imposing baddie in the Netflix Korean series Sweet Home and then The Predator in Prey, in addition to roles in Guardians of the Galaxy Vol. 3, Imaginary, Star Wars: Skeleton Crew, V/H/S/Beyond and Werewolves — though he has joked that he’d like to “play a human” someday as he expands his career.
The source notes that Olivia is very happy with Dane, adding that for Harry, “it’s just a massive relief to see that she’s finally met someone new.”
“He still cares about her and wants to see her happy.”
