Harry Styles and Olivia Wilde have crossed the fine line between lovers and exes.
On Nov. 18, E! News confirmed to E! News that the couple were putting a pause on their relationship after about two years of dating. News of the breakup came less than two months after the release of Don't Worry Darling, which Olivia directed and starred alongside Harry and Florence Pugh.
The notoriously private pair were first romantically linked in January 2021, when they looked awfully coupled up holding hands at a wedding for Harry's manager Jeff Azoff. And though the Harry and Olivia remained tight-lipped about their romance to the press, they became more comfortable with stepping out together as time went on. In fact, Olivia was sometimes seen dancing in the crowd at Harry's Love On Tour shows, with the most recent sighting at the singer's Nov. 15 concert in Los Angeles.
During their relationship, Harry and Olivia also took their love overseas with a romantic getaway to Italy. In July 2021, the One Direction alum and the Booksmart director weren't afraid to pack on a little PDA and were snapped kissing as they lounged on a boat together.
However, when it came to work, Harry and Olivia kept things strictly professional. At Don't Worry Darling's Venice Film Festival premiere in September, the duo opted not walk the red carpet as a couple and instead posed for a group shot with actress Sydney Chandler between them. They also sat apart during the screening of the film, with co-star Chris Pine acting as their buffer.
Nonetheless, Harry and Olivia made plenty of (midnight) memories throughout their romance. Keep scrolling to see some of their public outings during the golden relationship.
The pair got close while working on the thriller Don't Worry Darling. Harry was photographed visiting director and co-star Olivia's trailer on the set in Los Angeles in the fall of 2020.
More than a year after confirming their off-screen romance at a friend's wedding, the couple was out and about in London's Soho neighborhood in March 2022, matching in shades of blue.
That's amore! Harry and Olivia grabbed a bite to eat at Rubirosa, an Italian restaurant in New York, in August 2022.
The pair stepped out for a group photo at the Venice Film Festival to promote Don't Worry Darling, officially marking their first red carpet moment together (alongside Gemma Chan and Chris Pine, but still).
The duo, along with co-star Sydney Chandler, posed for a photo on the red carpet at the 79th Venice International Film Festival in September 2022.
Following a viral moment at the Venice Film Festival, Harry and Olivia both weighed in on rumors that Harry spit on Chris while taking their seats in the theater. The verdict? Chris' rep shut down the spitgate allegation, denying anything went wrong during the premiere.
The singer and actress headed into The Bowery Hotel together for an after-party in New York in September 2022. Two months later, E! News confirmed they were going their separate ways.