Harry Styles & Olivia Wilde’s Relationship Timeline is… Wilde

And the award for the most unexpected celeb couple goes to...
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Harry Styles, 27, and Olivia Wilde, 37, (or Holivia, as they have been dubbed), have made many headlines since they first sparked dating rumours.

WATCH: Harry Styles performs Watermelon Sugar at the Grammys 2021

Who would have thought that the former One Direction singer would end up dating Jason Sudeikis’ ex-partner?

Enter a psychological thriller film directed by Olivia and starring Harry and next thing you know the pair are vacationing in Italy together. It’s… dare we say it…. Wilde.

So just how did this relationship come to be, and where does Holivia stand these days? Scroll on to find out.

In 2020, Holivia was born. (Credit: Getty)

Late 2020 | Harry & Olivia team up for Don’t Worry Darling

Harry and Olivia were originally linked due to their joint involvement in the American Psychological thriller Don’t Worry Darling, directed by Olivia herself. Harry is playing the part of Jack, husband to Alice (played by Gen Z’s comfort person, Florence Pugh).

The 37-year-old was previously engaged to Ted Lasso star Jason Sudeikis with whom she shares two children, Otis and Daisy. The pair began dating in 2011 and got engaged in 2013, before a source revealed they split in 2020.

January 2021 | Harry & Olivia are spotted together at a wedding

In January 2021, Harry and Olivia were spotted attending Harry’s manager Jeff Azoff’s wedding in California.

In photos shared by Page Six that nearly broke the internet, the pair looked extremely fashionable as they strolled hand-in-hand through a garden.

Harry was dressed in a black tuxedo with a white lace undershirt and black ribbon bow; he was holding a fancy glass of alcohol in one hand and his date in the other. Olivia, meanwhile, sported a gorgeous bohemian peasant-style floral dress and baby pink headband.

The pair topped it off with matching face masks by The Vampire’s Wife.

Olivia penned a touching tribute to Harry after filming wrapped for Don’t Worry Darling. (Credit: Instagram)

February 2021 | Olivia pens a sweet Instagram tribute to Harry

For the most part, both Harry and Olivia have refrained from commenting on their relationship, save from the director’s Instagram tribute to the Kiwi singer back in February after filming wrapped.

Sharing a black-and-white photo of the 27-year-old atop a vintage car, Olivia 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. 👊”


July 2021 | Holivia’s Italian vacation sends Twitter into a frenzy

Cut to July 2021 and Holivia almost breaks the internet once more as they are spotted having a, what fans deemed, ✨ hot girl summer ✨ in Italy.

Soon after Harry wrapped filming for the film My Policeman, the beauty brand owner clearly thought he’d make the most of his time in Italy with a romantic vacation.

In photos obtained by Page Six, he and Olivia were spotted dancing and kissing on a Yacht in Monte Argentario.

September 2021 | Olivia supports Harry on his opening night of tour

On the opening night of Harry’s Love On Tour in Las Vegas, Olivia was his number one supporter.

Fans waved to the Booksmart director as she watched her beau’s first performance.

When the audience was so taken with Olivia that they almost missed Harry’s entrance, the actress promptly pointed towards the stage. Queen behaviour.

And it wasn’t just the first tour date that Olivia attended, with the actress making appearances for many of Harry’s shows across the States, even dancing alongside her children and Harry’s family. 

December 2021 | Olivia reps Harry’s new beauty brand

Get you a partner that will rep your beauty brand for the paps 😍😍.

Early this December, Olivia was spotted in LA sporting a jumper from Harry’s newly launched Pleasing brand. OK free marketing!!

The director has previously been sighted wearing Harry’s Treat People With Kindness merch and holding a Love On Tour tote bag – we’re just saying, she really should be charging the fruit man for this kind of promo.

BTW, we did a cheeky stalk and found out the black Pleasing crewneck is $143 Australian dollars. Sighs… opens wallet. NVM, it’s sold out – which is a loss for our wardrobe, but a win for our bank accounts. 

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