Since reaching the dizzy heights of fame with One Direction, Harry Styles has carved a unique solo career out of music, winning a Grammy for his single ‘Watermelon Sugar‘; acting, including his newest role in My Policeman alongside Emma Corrin; and fashion, as one of the stylish men, ever.
Naturally, when rumours began to circulate about his relationship with actor and director Olivia Wilde, some fans (possibly the same ones who used to bring ‘I Wanna Marry Harry’ placards to One Direction gigs) were devastated. But there’s no need to be upset: Olivia is a multi-talented (and award-winning) woman, with roles in The O.C. and Disney’s Tron: Legacy, as well as directing the critically-acclaimed Booksmart. You have to admit, they make a phenomenally cool couple.
The pair confirmed their romance earlier this year (2021), after they were spotted holding hands at a friend’s wedding. Since then, we’ve been oh-so invested in the development of their relationship, from praising each other on social media, to frolicking together on a yacht. Yep, they really are living their best lives.
Case in point: they were most recently spotted wandering through LA looking *very* in sync. With their arms draped around each other, Harry and Olivia both wore a white t-shirt, cut-out jeans, sunglasses, trainers, and a long necklace – serving major laidback (and loved-up) vibes.
Here’s everything we know about Harry and Olivia’s relationship timeline so far, from meeting on the set of Don’t Worry Darling to dishing out the PDAs in LA:
September 2020: Harry Styles is cast in Olivia Wilde’s new movie Don’t Worry Darling
Deadline reports that Harry has replaced Shia LaBeouf in one of the lead roles for Olivia’s film Don’t Worry Darling. It’s the second film she’s directed (after Booksmart), and she took to Instagram to celebrate the casting of Harry and Florence Pugh in the film’s lead roles, saying, “Very proud to work with these fine folks.”
13 November 2020: Olivia praises Harry in an interview
In an interview with Vogue, Olivia described her and costume designer Arianne Phillips’ reaction to casting Harry, saying (via People), “She 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.
“And this movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that [Harry] is so enthusiastic about that element of the process-some actors just don’t care.”
Olivia continued, “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.
“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.”
13 November 2020: Reports emerge that Olivia Wilde and fiancé Jason Sudeikis have separated
People report that Olivia Wilde and Jason Sudeikis have ended their engagement after seven years together. A source told People, “The split happened at the beginning of the year. 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.
Olivia and Jason have two children together, Otis Alexander and Daisy Josephine.
Entertainment Tonight confirmed the split, saying, “They just fell out of love in a romantic way, but still have love towards one another as people. They consider themselves friends and co-parents first and foremost.”
Another source added, “There was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.”
16 November 2020: Olivia hits back at Candace Owens after she criticised Harry’s dress sense
After Harry Styles wore a Gucci dress on the cover of Vogue, author Candace Owens tweeted: “There is no society that can survive without strong men. The East knows this. In the west, the steady feminization of our men at the same time that Marxism is being taught to our children is not a coincidence.
It is an outright attack.
“Bring back manly men.”
Olivia’s reply was spot on, tweeting, “You’re pathetic.”
4 January 2021: Harry and Olivia are spotted holding hands at a wedding
Page Six obtains photos of Harry and Olivia holding hands at his agent – Jeffrey Azoff’s – wedding. Around the same time, People report that the pair “were affectionate around their friends, held hands and looked very happy,” confirming that, “they have dated for a few weeks.”
5 January 2021: It’s reported that Harry referred to Olivia as his girlfriend during a wedding speech
A source tells Page Six that Harry has been introducing Olivia as his girlfriend, reportedly saying, “A source said, “This relationship between Harry and Olivia is very new. Olivia has been directing Harry in the movie in Palm Springs, and there were literally 10 people on the set, because they were strictly adhering to COVID rules.
“Harry had been staying at James Corden’s house near Palm Springs during filming, and so they were able to be alone and keep their relationship very secret.
“So everyone was really surprised – and rather delighted – when Harry brought Olivia as his date to the wedding, and introduced her as his girlfriend.”
9 January 2021: A source reports that Harry and Olivia initially kept their relationship ‘under wraps’
US Weekly reported that an insider revealed, “Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge. They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”
22 January 2021: A source reports that Harry and Olivia’s relationship isn’t a PR stunt
According to Entertainment Tonight, a source reports that the photos of Olivia and Harry holding hands are not staged, suggesting that their relationship is very much the real deal, saying, “[The wedding photos were] absolutely not leaked or staged for some sort of promotional reason.”
6 February 2021: Harry and Olivia are reportedly very happy together
A source tells People that Harry and Olivia “seem very serious” and “spend all their time together” as they continue to shoot Don’t Worry Darling. The source added that Olivia is “very happy with Harry,” adds the source.
14 February 2021: Olivia shares sweet tribute to Harry on Instagram
Olivia posted a picture of Harry reclining on a car with a very cute caption, praising him for playing a supporting role in a female-led project. She wrote:
“Little known fact: most male actors don’t want to play supporting roles in female-led films. 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” . Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our “Alice”, but he infused every scene with a nuanced sense of humanity. 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.”
February 2021: Olivia and Jason Sudeikis are reportedly on better terms
Entertainment Tonight report that, according to an insider, “Jason was initially really hurt about Harry and Olivia’s relationship, but now that he’s doing his own thing, things between him and Olivia have gotten better. They’re rebuilding their friendship again and co-parenting together.”
16 March 2021: Olivia posts a not-so-subtle tribute to Harry on Instagram following his Grammy win
After Harry won his first Grammy for Best Pop Solo Performance for his single, ‘Watermelon Sugar’ Wilde appeared to offer a subtle form of congratulations on her Instagram Stories. She posted a snap of Paul McCartney tucking into a watermelon, which is clearly a reference to Harry’s hit song, right?
4 June 2021: It’s reported that Harry and Olivia are getting closer as a couple
According to ET Online, a source reported that Harry and Olivia have been “having an awesome time” in London together. Adding that they’ve been “going on walks outside in the park and not hiding their relationship,” and have “grown even closer as a couple.”
The source continued,”Yesterday, they enjoyed lunch outside and looked incredibly cute together. They were both in a great mood and left the restaurant holding hands. Harry put his arm around Olivia as they walked back to her house.”
A second source added, “Harry and Olivia have been inseparable. Of course that’s in part because they’ve been in a bubble for their film, but even in the days since it wrapped, they’re still spending all their time together.”
5 July 2021: Harry and Olivia are spotted frolicking on a yacht
Page Six obtains photos of Harry and Olivia making out on a yacht in Italy. Jealous? Us?
Keep the PDAs coming, guys!