Who is Harry Styles Dating: Their Relationship Timeline!
The stars met on the set of Don’t Worry Darling and first appeared together in January 2021.
Harry Styles and Olivia Wilde’s relationship is still going strong after more than a year. The 38-year-old filmmaker and the 28-year-old singer, who met on the set of their film Don’t Worry Darling in September 2020, first appeared as a couple in January 2021 while attending a wedding together. “What began as a close friendship quickly turned romantic,” a source told PEOPLE exclusively at the time. “Everyone predicted it. He hasn’t been able to stay away from her trailer during his breaks.”
In February 2021, a source told PEOPLE that the couple appeared “very serious” and spent “all their time together” on the Don’t Worry Darling set. “She is also very happy with Harry,” the actress’s source added. An insider previously told PEOPLE that Wilde split from her seven-year fiancé, Jason Sudeikis, in early 2020. Here’s everything you need to know about Harry Styles and Olivia Wilde’s relationship, from their on-set chemistry to their PDA-filled getaway.
September 2020: Harry Styles joins the cast of Olivia Wilde’s film Don’t Worry Darling
Styles joined the cast of Don’t Worry, Darling in September 2020, replacing Shia LaBeouf, who was set to play a supporting role alongside Florence Pugh in the Wilde-directed film.
Deadline reported at the time that LaBeouf had to leave due to scheduling conflicts.
November 2020: PEOPLE reports that Olivia Wilde and Jason Sudeikis ended their engagement
PEOPLE exclusively revealed in November that Wilde and her longtime fiancé, Jason Sudeikis, with whom she shares son Otis and daughter Daisy, had split up.
“The split happened at the beginning of the year,” a source revealed at the time, explaining that the couple’s main priority was their children’s well-being. “It’s been amicable, and they’ve settled into an excellent co-parenting routine. The children are the family’s priority and the heart of the relationship “According to the source.
December 2020: Olivia Wilde says she’s blown away by Harry Styles’ acting chops
She also praised his lack of “toxic masculinity”. In Vogue, she said it’s “extraordinary” to see him redefining what it means to be a man with confidence.
January 2021: Harry Styles wraps his arm around Olivia Wilde
Styles upped the ante on their PDA just one day after photos of the couple walking hand in hand were released, wrapping his arm around Wilde while talking with friends in a parking lot.
February 2021: Olivia Wilde and Harry Styles pose for a cast and crew photo
Don’t be concerned. On wrap day, Darling star Ali Asif shared a group photo with members of the cast and crew. Styles was seen in the photo with his arm around Wilde as they smiled alongside Asif, Pugh, Nick Kroll, Kate Berlant, and members of the crew.
Asif captioned the photo, “GIANTIC congratulations to EVERYONE involved in making this beautiful film during these very trying times.”
July 2021: Olivia Wilde and Harry Styles soak up the sun in Italy
The couple was photographed sharing a passionate kiss aboard a yacht in Monte Argentario, Italy, in July.
They were later seen kissing again while sunbathing before boarding a smaller boat to continue their date.
November 2021: Olivia Wilde wears Harry Styles’ tour shirt
The director stepped up her support for Styles in November, when she was spotted at an L.A. Starbucks wearing black leggings and a “Love on Tour” tee from her 2021 tour.
December 2021: Harry Styles gets to know Olivia Wilde’s kids
A source told PEOPLE that the couple was getting serious and spending time with each other’s families almost a year into their relationship.
“Harry is slowly getting to know her kids,” the source said, adding that “Olivia is also spending time with Harry’s mother.”
Despite their hectic schedules, the couple prioritises their time together, according to the source.
“Olivia has been flying nonstop between L.A., where her children live, and Harry’s tour,” an insider revealed. “She always appears to be preoccupied with making everything work. She is Harry’s number one fan.”
May 2022: Harry Styles and Olivia Wilde step out in Italy
The couple was photographed together in Italy on May 10 ahead of the singer’s Love on Tour concerts. The appearance came about two weeks after Wilde was served custody papers by ex Jason Sudeikis on stage during her April presentation at CinemaCon in Las Vegas.
September 5, 2022: Olivia Wilde and Harry Styles attend the Venice Film Festival premiere of Don’t Worry Darling
Both Wilde and Styles attended the Venice Film Festival premiere of Don’t Worry Darling, though fans pointed out that they were not seated together.
Styles made headlines after a video of him taking his seat next to his co-star, Chris Pine, went viral. Styles moves his lips before Pine looks down and appears to giggle in the video, which some believe indicates Styles spitting on Pine. Wilde is seated on the opposite side of the Star Trek actor in the video.
Styles and Wilde were photographed together earlier that day while posing for a cast photo alongside Pine, Pugh, Gemma Chan, Sydney Chandler, and Nick Kroll, though they did not stand next to each other.
Harry Styles and Olivia Culverhouse director were spotted together in Los Angeles. The couple attended a Wolf Alice concert. She wore an outfit from Harry’s nail polish and skincare brand Pleasing. The Don’t Worry Darling director gave a subtle nod to her man with a sweatshirt.