Harry Styles and Olivia Wilde's Relationship Timeline (2024)

Nearly two years into their relationship, Harry Styles and Olivia Wilde are "taking a break."

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.

In November 2022, however, multiple sources confirmed to PEOPLE that Styles and Wilde are taking some time apart. Just days after Wilde was spotted at the singer's concert with her children, a source told PEOPLE that the pair "have different priorities that are keeping them apart."

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

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

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

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

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

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

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.

May 30, 2022: Harry Styles and Olivia Wilde are "more serious than ever"

A source told PEOPLE that Styles and Wilde are "more serious than ever" in May 2022.

The source said they'd been "finding ways to make things work" amid busy schedules, adding, "What might have seemed like a fling initially, is now a committed relationship."

"Harry is very smitten," the insider continued. "Olivia has very much brought out his romantic side. He also has tremendous respect for her when it comes to work. He would love to work with her again. They both support each other's careers."

August 22, 2022: Harry Styles talks to Rolling Stone about keeping his sexuality and relationships private

In an interview with Rolling Stone, Styles spoke about his choice to protect his romantic relationships from the public.

"I've never talked about my life away from work publicly and found that it's benefited me positively," he told the outlet. "There's always going to be a version of a narrative, and I think I just decided I wasn't going to spend the time trying to correct it or redirect it in some way."

Styles also spoke about fan speculation toward his sexuality, and how he doesn't think his seemingly public romances should define him.

"Sometimes people say, 'You've only publicly been with women,' and I don't think I've publicly been with anyone," he said.

Wilde was also quoted in the cover story and spoke to the outlet about her experience with Styles' zealous fans. Despite receiving hate online for her relationship with the singer, Wilde referred to Styles' supporters as "deeply loving people."

"What I don't understand about the cruelty you're referencing is that that kind of toxic negativity is the antithesis of Harry, and everything he puts out there," she said. "I don't personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness."

August 24, 2022: Olivia Wilde says she and Harry Styles are protective of their relationship

Wilde spoke to Variety about collaborating with Styles on her upcoming film Don't Worry Darling, but stated that she's "not going to say anything about" her relationship with the singer "because I've never seen a relationship benefit from being dragged into the public arena."

"We both go out of our way to protect our relationship," she said. "I think it's out of experience, but also just out of deep love."

Wilde also said she thinks there's a double standard that criticizes her for dating a younger man and labels her an absentee mother: "When people see me not with my kids, it's always 'How dare she.' I've never seen anyone say that about a guy. And if he is with his kid, he's a f---ing hero."

September 5, 2022: Olivia Wilde and Harry Styles attend the Venice Film Festival premiere of Don't Worry Darling

Wilde and Styles both attended the Venice Film Festival premiere of Don't Worry Darling, though fans pointed out that they were not sitting together at the film's screening.

Styles made headlines when a clip began circulating of the singer taking his seat next to his costar, Chris Pine. In the video, Styles moved his lips before Pine looked down and appeared to giggle, which some believe signified Styles spitting on Pine. In the clip, Wilde is seated on the other side of the Star Trek actor.

Earlier that day, Styles and Wilde were photographed together while posing for a cast photo with Pine, Pugh, Gemma Chan, Sydney Chandler and Nick Kroll, though they did not stand next to each other.

September 8, 2022: Olivia Wilde says she "instantly started crying" when she saw Harry Styles perform

In a cover story for Vanity Fair, Wilde spoke about her relationship with Styles and addressed rumors that she left Sudeikis for the musician.

"The complete horses--- idea that I left Jason for Harry is completely inaccurate," she said. "Our relationship was over long before I met Harry."

Wilde also discussed why she tries to keep details of her romance with Styles private. "I think once you crack open the window, you can't then be mad when mosquitoes come in," she explained. "It's like, 'You opened the window.' "

The director went on, sharing details from a night when she watched Styles perform at a 21,000-person arena. Wilde recalled standing with indie rock icon Jenny Lewis, who opened the show, during his performance.

"We were looking around, and she said, 'That's a lot of happy women,' " she recalled. "I instantly started crying. Where else do we see this? Happy women? Women brought together with joy, loving each other, and cheering for each other? This has been like a gift to be amongst this."

Wilde mentioned that Styles' fans have welcomed her with open arms: "His fans are a beautiful and loving group of people. I have had the opportunity to witness some of the most moving examples of compassion and acceptance."

September 21, 2022: Olivia Wilde attends Harry Styles' final Madison Square Garden concert

Styles' 15-show residency at Madison Square Garden in N.Y.C. came to an end — and Wilde was there to celebrate his successful run of sold-out concerts.

Fans spotted the Don't Worry Darling director dancing and singing as Styles performed. She donned a white maxi dress and a feather boa, which has become a staple accessory for fans at the singer's shows.

That same day, the couple were seen kissing on the street in N.Y.C. Their evening outing came one day before the theater premiere for their film Don't Worry Darling.

October 17, 2022: Olivia Wilde and Jason Sudeikis' former nanny claims Harry Styles' music was "banned" from their home

In an interview with the Daily Mail, one of Wilde and Sudeikis' former nannies shared alleged details about the pair's split and the beginnings of Wilde's relationship with Styles. The nanny, who was not named, claimed that Sudeikis was blindsided and "brokenhearted" by Wilde's new relationship, saying that the father of two did "a lot of crying" after learning of the romance.

The nanny alleged that Sudeikis tried to prevent Wilde from going to see Styles by lying down in front of her car so she wouldn't leave. According to the nanny, the Ted Lasso star became upset after seeing Wilde prepare a salad, allegedly for Styles, with her "special dressing" in the family's kitchen.

The nanny also claimed that Sudeikis discovered details of Wilde's relationship with Styles on an Apple Watch she left behind while filming Don't Worry Darling that contained messages between the pair and that, after learning of the relationship, Sudeikis banned them from playing Styles' music.

In a joint statement to PEOPLE, Wilde and Sudeikis denied their former employee's claims, calling the accusations "false and scurrilous."

October 21, 2022: Olivia Wilde and Harry Styles are "thriving" despite nanny's claims

Wilde and Styles aren't letting any drama get in the way of their happiness.

"Harry and Olivia are great. They're better than ever. They rise above this sort of thing all the time, and they're just moving forward with their relationship and are happy and thriving," a source told PEOPLE.

The insider added that Wilde "is happy that Harry is around" as she deals with the situation. "All the drama is a lot and definitely affects her," the source said.

A separate Styles source acknowledged that the "controversy surrounding their relationship and movie", Don't Worry Darling, hasn't been easy for the musician, but he isn't focusing on the drama.

"He likes to live a pretty care-free, happy life. Olivia has been stressed about [the drama] and it affects Harry too," said the Styles source. "But he has been very focused on enjoying their special relationship."

November 15, 2022: Olivia Wilde brings her kids to Harry Styles' concert

Wilde attended one of Styles' Los Angeles shows with her son and daughter, Otis and Daisy, by her side. Fans spotted the mom of two settling into her seat at the venue and dancing with Daisy to Styles' hit "As It Was."

November 18, 2022: Olivia Wilde and Harry Styles are "taking a break"

After nearly two years together, Wilde and Styles are pressing pause on their romance. Multiple sources confirmed exclusively to PEOPLE that the pair are "taking a break" from their relationship.

"He's still touring and is now going abroad. She is focusing on her kids and her work in L.A.," one source said. "It's a very amicable decision."

"They're still very close friends," the insider added.

November 22, 2022: Olivia Wilde finds the "break" from Harry Styles to be "difficult"

While the decision to spend time apart was amicable, a source told PEOPLE that "the break has been difficult for Olivia."

The source added: "They have had some issues, but Olivia thought they were gonna work through it all. She is disappointed. It's just a tricky situation, though."

February 23, 2023: Source says Olivia Wilde and Harry Styles remain "good friends"

A source told PEOPLE that Wilde is in a "good place" following her very public breakup with Styles.

"She's focused on her kids and co-parenting with Jason," the insider said. "She and Harry are good friends, there's no animosity whatsoever. Plus, she's got many different directing projects in the works."

July 28, 2023: Harry Styles shows off his "Olivia" tattoo

While on a yacht in Italy, Styles wore a pair of ultra-short swim trunks that revealed his leg tattoos. "Olivia" spelled in large cursive letters could be seen on his right thigh —and fans speculated that the tattoo was dedicated to Wilde.