Apparently Olivia Wilde Has Moved on to Some Guy Named Harry Styles

Every once and awhile the public is thrown for a loop when an unlikely and random couple emerge onto the scene. We’ve seen tons of pairings, from Billy Bob Thornton and Angelina Jolie to Scott Disick and Amelia Gray Hamlin, that have made us scratch our heads and wonder how they ever got together. 

While Olivia Wilde and Harry Styles make sense as far as physical attraction goes (they’re both extremely good-looking), they do have a large age difference that has made people wonder what the two have in common. 

At first, it’s pretty normal to wonder how an international pop singer and an indie movie director and actress would ever cross paths, but once we go into the detail about how these two connected, it makes a lot more sense. Olivia produced and directed the film Don’t Worry Darling starring Florence Pugh, Chris Pine, and, you guessed it, Harry Styles. The psychological horror film is the first full length feature Olivia has directed since the critically acclaimed film Booksmart.

The film tells the story of a suburban housewife who discovered a dark secret. Harry Styles plays Florence Pugh’s husband in the film. According to Cinema Blend, the role was originally set for Shia LaBeouf, but, after many personal conflicts and differences in opinion, Olivia moved on from Shia and ended up choosing Harry for the role instead. 

Olivia, 36, and Harry, 26, were spotted holding hands at his agent’s wedding at the San Ysidro Ranch in Montecito, Calif. over the first weekend of January 2021 in exclusive photos obtained by Page Six. “Although Wilde appears to typically prefer older men — she was married for eight years to filmmaker Tao Ruspoli, who like Sudeikis is nine years her senior — Styles is no stranger to dating older women,” the outlet reported. 

While Olivia may not be the first older woman that Harry has dated, she may be the first to have children. The House actress shares a 6-year-old son, Otis, and 4-year-old daughter, Daisy, with Jason Sudeikis. Olivia was partnered with Jason from 2011 to 2020. The two reportedly ended their engagement at the beginning of 2020.

"The split happened at the beginning of the year," a source close to the couple told People. "It's been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship." 

Ever since Harry Styles became the fan-favorite member of One Direction, people have been speculating who the singer is dating. Some of the more popular names that Harry has been linked to include Kendall Jenner and Taylor Swift. He made headlines when late former girlfriend and Love Island host Caroline Flack spilled all the tea about the two in her book. 

“I already knew that he had a crush on me, he’d made it pretty obvious,” she said in her autobiography, Storm in a C Cup. “He’d said it in magazines and he’d said it to friends.” Harry was 17 years old at the time, and Caroline was 31, which caused a lot of gossip and controversy. The accusations allegedly caused the pair to go their separate ways.