People.com Entertainment Music Harry Styles and Olivia Wilde's Relationship Timeline The stars first met on the set of Don’t Worry Darling and stepped out as a couple in January 2021 By Nicole Briese Nicole Briese Contributor, PEOPLE People Editorial Guidelines Updated on May 24, 2022 12:29 PM Share Tweet Pin Email Photo: BACKGRID More than a year into their relationship, Harry Styles and Olivia Wilde are still going strong. The 38-year-old filmmaker and the 28-year-old singer — who first met on the set of their film Don't Worry Darling back in September 2020 — stepped out as a couple while attending a wedding together in January 2021. "What started out as a close friendship, quickly turned romantic," a source exclusively revealed to PEOPLE at the time. "Everyone saw it coming. During breaks, he hasn't been able to stay away and visited her trailer." A source also told PEOPLE in February 2021 that the couple seemed "very serious" and spent "all their time together" on the Don't Worry Darling set. "She is also very happy with Harry," added the source of the actress. Wilde split from her fiancé of seven years, Jason Sudeikis, in early 2020, an insider previously told PEOPLE. From their on-set sparks to their PDA-filled getaway, here's everything you need to know about Harry Styles and Olivia Wilde's relationship. September 2020: Harry Styles joins the cast of Olivia Wilde's film Don't Worry Darling Styles joined the Don't Worry Darling cast in September 2020, signing on to replace Shia LaBeouf, who was slated to star in a supporting role alongside Florence Pugh in the Wilde-directed film. At the time, Deadline reported that LaBeouf had to depart due to scheduling conflicts. November 2020: PEOPLE reports that Olivia Wilde and Jason Sudeikis ended their engagement In November, PEOPLE exclusively learned that Wilde and her longtime fiancé, Jason Sudeikis, with whom she shares son Otis and daughter Daisy, had gone their separate ways. "The split happened at the beginning of the year," a source revealed at the time, explaining that their children's wellbeing was the pair's main focus. "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," the source said. December 2020: Olivia Wilde says she's blown away by Harry Styles' acting chops Harry Styles, Olivia Wilde. getty (2) Wilde had nothing but praise for her new male lead in Styles' Vogue profile, telling the publication that his turn as Alex in 2017's Dunkirk blew her away. "[Costume designer Arianne Phillips] and I did a little victory dance when we heard that we officially had Harry in the film because we knew that he has a real appreciation for fashion and style," she said. As Wilde explained, Styles' knack for all things sartorial would be key to playing Jack in her film. "This movie is incredibly stylistic. It's very heightened and opulent, and I'm really grateful that he is so enthusiastic about that element of the process — some actors just don't care." Beyond his style, Wilde called out Styles' lack of "toxic masculinity." "To me, he's very modern, and I hope that this brand of confidence as a male that Harry has — truly devoid of any traces of toxic masculinity — is indicative of his generation and therefore the future of the world," she told the publication, adding, "I think he is in many ways championing that, spearheading that. It's pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence." January 2021: Olivia Wilde and Harry Styles are seen holding hands Backgrid The Life Itself actress and the former X-Factor hopeful had the internet abuzz in January 2021, when they were photographed holding hands at Styles' agent's wedding in Montecito, California. "They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks," a source told PEOPLE at the time. January 2021: Harry Styles wraps his arm around Olivia Wilde Just one day after photos were released of the couple walking hand in hand, Styles upped the ante on their PDA, wrapping his arm around Wilde while talking with friends in a parking lot. February 2021: Olivia Wilde praises Harry Styles' modesty One month after the duo made headlines with their budding romance, Wilde gave her new beau major props via social media. "Little known fact: Most male actors don't want to play supporting roles in female-led films," she captioned a photo of Styles wearing a suit while sitting on top of a shiny black car. She continued, "The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it's so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our 'Jack.' " The director also said that Styles gave star Florence Pugh the room to shine in her own right. "He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards," she wrote. February 2021: Olivia Wilde and Harry Styles pose for a cast and crew photo Asif Ali/Instagram Don't Worry Darling star Ali Asif shared a group photo with members of the cast and crew on wrap day. In the shot, Styles was seen with his arm around Wilde as they smiled beside Asif, Pugh, Nick Kroll, Kate Berlant and members of the crew. "GIGANTIC congratulations to EVERYONE involved in making this beautiful film during these very trying times," Asif captioned the photo. February 2021: Olivia Wilde and Harry Styles travel to England With Don't Worry Darling complete, a source revealed to PEOPLE that the couple, who had been staying together in Styles' Hollywood home, had headed to England. July 2021: Olivia Wilde and Harry Styles soak up the sun in Italy Backgrid In July, the couple vacationed in Monte Argentario, Italy, where they were photographed sharing a passionate kiss aboard a yacht. They were later seen kissing once more while sunbathing before they made their way onto a smaller boat to continue their date. September 2021: Olivia Wilde dances at Harry Styles' concert Wilde, dressed in a loose-fitting baby blue suit, was seen dancing in the front row of Styles' concert at the MGM in Las Vegas in September. "She was so happy and dancing all night!" a concertgoer told E! News. "It was very cute. She was singing along to almost every song and having a good time with the people she was with." November 2021: Olivia Wilde supports Harry Styles' new beauty line Olivia Wilde/Instagram After the former One Direction member debuted his unisex nail polish, Pleasing, in November, Wilde was quick to show her support for her significant other's new business venture. "I find this very pleasing," she cheekily captioned a plug for the brand on Instagram. November 2021: Olivia Wilde wears Harry Styles' tour shirt The director doubled down on her support in November, when she was spotted at an L.A. Starbucks in a pair of black leggings and a "Love on Tour" tee from Styles' 2021 tour. December 2021: Olivia Wilde addresses the attention on her relationship with Harry Styles In December, Wilde briefly spoke about the spotlight on the couple's relationship in a cover story for Vogue's January 2022 issue. "It's obviously really tempting to correct a false narrative," she told the outlet of the attention surrounding their romance. "I think what you realize is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love." She concluded, "I'm happier than I've ever been. And I'm healthier than I've ever been, and it's just wonderful to feel that." December 2021: Harry Styles gets to know Olivia Wilde's kids Almost a year into their relationship, a source revealed to PEOPLE that the twosome was getting serious and spending time with each other's families. "Harry is slowly getting to know her kids," the insider revealed, adding, "Olivia is also spending time with Harry's mom." The source also shared that the pair was prioritizing their time together despite their busy schedules. "Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour," the insider revealed. "She always seems focused on just making it all work. She is really Harry's biggest fan." February 2022: Olivia Wilde celebrates Harry Styles' 28th birthday Olivia Wilde; Harry Styles. Rachel Murray/Getty; Dia Dipasupil/Getty In February, Wilde donned the floral jumpsuit of her "dreams" to celebrate Style's 28th birthday. The director shared two snaps on Instagram from the festivities. "Happy happy," she captioned one of the photos that showed her standing behind a candlelit table. January 2022: Olivia Wilde supports Harry Styles' new movie When Styles' Eternals costar, Gemma Chan, shared a series of photos of herself and the actor all suited up as their respective characters of Stersi and Starfox in January, Wilde was quick to add her support. "Watching now obviously," she commented, adding a series of raised hands emojis. April 2022: Harry Styles releases a new song — and fans speculate it's about Olivia Wilde Styles released his first song in more than two years in April 2022 with "As It Was," and lyrics from the track had the internet speculating that at least one line referenced Wilde. The part in question? "I don't wanna talk about the way that it was, leave America, two kids follow her, I don't wanna talk about who's doin' it first." April 2022: Harry Styles reveals he's "really happy" amid his relationship with Olivia Wilde Later that month, Styles told SiriusXM's The Morning Mash Up that the process of creating his upcoming album Harry's House has been "the most joyous of anything" he's experienced while making music so far. "I feel the most comfortable I've been with myself and happiest with what I'm making and the best I felt about something that I'm making," he said, explaining that he's happy with the music and with his life, which will be reflected in his new work. "I also feel really happy at the moment and I feel like it's the first time I feel like I'm making music and putting music out from a real place of personal freedom," he shared. "And that is a really liberating place to [be] creating from and now putting it out." May 2022: Harry Styles and Olivia Wilde step out in Italy On May 10, the couple was photographed in Italy together ahead of the singer's Love on Tour concerts. The outing came about two weeks after Wilde was served custody papers from ex Jason Sudeikis on stage in the middle of her presentation at CinemaCon in Las Vegas in April. May 2022: Harry Styles talks about being directed by Olivia Wilde in Don't Worry Darling In an interview with Howard Stern for the latter's SiriusXM show, Styles was asked, "You fell in love on a movie set?" Though Styles played coy about discussing his love life, he did praise Wilde as a director, adding, "I had a wonderful experience being directed by Olivia. I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot." He also noted, "Being able to trust your director is a gift. That was very helpful, and it really meant for a really nice experience working on that movie," Styles said.