Harry Styles and Olivia Wilde surprised fans with their fiery relationship after ‘growing close’ on the set of psychological thriller Don’t Worry Darling.
The former One Direction heartthrob, 28, and Hollywood actress Olivia Wilde, 38, sparked an instant connection when Harry joined the film which Olivia was directing.
The duo made headlines when they were pictured holding hands at a wedding in January of 2021, following Oliva’s split from former fiancé and Ted Lasso actor Jason Sudeikis, 46, just two months prior.
Although they they tried to keep their relationship a secret, their 10-year age gap romance began to heat up and the two could no longer hide the fact that they were a couple, the singer even described it as the ‘most serious’ relationship he’s ever been in.
Here’s a look at a timeline of the couple’s relationship…
June 14, 2022: Harry carries Olivia’s bags as they stroll through London
Harry proved that he was still the doting boyfriend as he carried his girlfriend Olivia’s bags (actress seen right) during a stroll through London
Harry Styles kicked off his much anticipated Love On Tour and his girlfriend Olivia Wilde joined him as they strolled through west London. The singer proved he was still a chivalrous boyfriend as he carried Oliva’s tote bags while she followed behind him.
The One Direction alum kept it casual and wore a grey sweatshirt and blue baseball cap during his much needed break from tour with his lover who is ten years his senior, Olivia.
June 10, 2022: Harry and Olivia check out properties together
Harry and Olivia are seen hand in hand while viewing properties in Hampstead, North London
The couple appeared to be making plans to move into a new home together as they checked out properties while strolling through London. Harry was seen examining the details of homes for sale in the window of an estate agent’s in Hampstead with Olivia at his side.
Although the couple strolled to the estate agent’s office they couldn’t enter as it closed for the evening, but it doesn’t look like it will stop Harry and Olivia as their relationship seems to be heating up.
May 22, 2022: Harry and Olivia jet out of New York City
Olivia and Harry kept it low key as they walked through the airport in New York on their way to catch a flight
Harry and Olivia sported low key outfits while on their way to catch a flight out of NYC. The 28-year-old singer and 38-year-old actress attempted to go incognito while at the airport and were barley recognizable.
The singer wore a pair of dark wash jeans, a white t-shirt, black coat, mask and sun glasses. The Grammy award winner also pulled his hair into a top bun. Olivia wore jeans, sneakers, a gray t-shirt and black jacket. The actress and director paired her low key look with a mask, sunglasses and wore her hair in loose layers.
May 18, 2022: Harry squirms when asked if he fell in love with Olivia on the set of their film
‘Oh, wow… how to answer this question?’: Harry Styles squirmed when asked directly if he fell in love with Olivia Wilde on the set of Don’t Worry Darling
On Sirius XM’s The Howard Stern Show, Harry gave a shy response to a question posed about falling in love with his girlfriend Olivia.
The singer said he had a ‘wonderful’ experience while being directed by Olivia on the set of psychological film Don’t Worry Darling. He was then asked if he fell in love with her while on the set.
‘Oh, wow… how to answer this question?’ he said on Sirius XM’s The Howard Stern Show. He added that trusting Olivia as his director was ‘very helpful.’
May 1, 2022: Olivia is served with custody papers while on stage and Harry blows off steam days after while hiking
Olivia Wilde was served with custody papers from her ex Jason Sudeikis while on stage at CinemaCon and her boyfriend was seen days later blowing off the steam while hiking
The singer was seen attempting to shrug off the headlines as he hiked with a friend through the hills of LA days after Olivia was served custody papers by her ex Jason Sudeikis while she was on stage at CinemaCon in Las Vegas.
Olivia was giving a presentation when she was served with legal papers pertaining to the children she shares with Sudeikis, 46, the actress paused to verify the documents were hers before continuing her presentation.
Sudeikis made a statement regarding his ex and said that he had ‘no prior knowledge of the time or place that the envelope would have been delivered.’ He added that he would never want her to be served in such an ‘inappropriate manner.’
April 18, 2022: Olivia cheers Harry on during headlining set at Coachella
Olivia Wilde cheers on boyfriend Harry Styles during his Coachella and proved she was his biggest fan while rocking out to Harry singing
It was no surprise to see Olivia cheering on her beau while he performed his headlining slot at Coachella musical festival in Indio, California.
The actress and director has proven herself to be Harry’s biggest fan; Olivia was spotted rocking out and dancing with his friends. One video showed Olivia in the audience smiling while Harry belted out his solo hit Sign of the Times.
March 21, 2022: Olivia sports Harry’s tour merchandise
Olivia Wilde showed she was a supportive girlfriend as she stepped out in London wearing her boyfriend Harry Styles’ tour merch
The actress showed her support for her boyfriend who is ten years younger than her as she wore his ‘Love On Tour’ tote bag while running errands in London. She stepped out wearing the oversized tote from Harry’s Madison Square Garden Show.
Olivia is said to be Harry’s ‘biggest fan’ and has always tried to make their relationship ‘work,’ the star’s outing came after reports the two were getting very ‘serious.’
February 3, 2022: Olivia wears ‘dream’ jumpsuit while celebrating Harry’s birthday
Olivia Wilde shared a mirror selfie with her 4million followers on Instagram as she rocked the chic one piece look from Kwaidan Editions while celebrating Harry’s birthday
The 37-year-old actress sported a stylish jumpsuit with sunflowers printed all over it to celebrate the 28th birthday of boyfriend.
The actress and director took to her Instagram to share a photo of her wearing a floral jumpsuit she described as a ‘dream.’
She also shared another photo of herself to her over four million followers standing next to a candle-lit dinner table with the caption: ‘happy happy.’
February 15, 2021: Olivia praises Harry in an Instagram post
Olivia Wilde paid tribute to her boyfriend Harry Styles after he starred in her upcoming movie, Don’t Worry Darling and said he blew her away with his ‘talent’ and ‘warmth’
The actress and director gushed over her boyfriend who is ten years younger than her on her social media as she paid tribute to the stars of her movie Don’t Worry Darling.
After production wrapped on her psychological horror movie, Olivia shared some of her favorite movie-making memories to Instagram, including a post dedicated to her new boyfriend.
The filmmaker wrote about how she admired Harry for accepting a supporting role alongside a female lead and gushed about the singer’s ‘talent’, ‘warmth’ and ‘grace’.
January 9, 2021: Olivia’s ex Jason Sudeikis is reportedly ‘heartbroken’ about the split
Jason Sudeikis was reportedly ‘absolutely heartbroken’ following split with actress Olivia Wilde
When Olivia and her fiancé Jason Sudeikis announced their split in November, they were reported to have gone their separate ways in early 2020.
However, a source close to the Ted Lasso actor claimed that the couple was actually together and the actor wasn’t aware Olivia wanted to call off their engagement until October, which is around the time her relationship with former One Direction heartthrob took off.
Jason was reportedly ‘absolutely heartbroken about the split’ and her and on-set romance with Harry.
December 9, 2021: Olivia addressed rumors regarding her split from her ex and surprise romance with Harry
Although Wilde appears to be moving on with her new leading man, she addressed the ‘false narratives’ and she and Sudeikis look to be on good terms as they co-parent their two kids; seen in 2018
Olivia addressed the ‘false narrative’ surrounding her relationship with Harry, who she went public with just two months after splitting with actor Jason Sudeikis.
When Olivia was seen holding hands with her beau Harry, who is a decade younger than her, many people raised an eyebrow at how quickly she moved on.
And while the actress said it was ‘tempting’ to correct the false narrative she added in her Vogue interview: ‘But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you.’
DECEMBER 21, 2021: Olivia introduces Harry to her two children
Harry Styles is reportedly ‘slowly’ getting to know the children of his girlfriend Olivia Wilde almost a year into their relationship
Almost a year into their relationship, the couple took the next step as Harry began ‘slowly’ getting to know the actresses’ children Otis, eight, and Daisy, five. At the same time Harry spent time with Otis and Daisy, Olivia began spending time with the singer’s mom.
The couple had been trying to spend as time together as possible after Harry finished his Harry finished his Love on Tour tour while Wilde wrapped the period drama Babylon with Brad Pitt and Margot Robbie.
November 8, 2021: Olivia is seen sporting Harry’s gold crucifix necklace
Olivia wore Harry’s favorite golden crucifix necklace, signaling he either lent it to her or gave it to her; the singer was last seen wearing the necklace on March 14
The award-winning filmmaker wore Harry’s favorite golden crucifix necklace, signaling he either gave it to her or lent it to her.
The 38-year-old rocked her touring 28-year-old toyboy’s necklace at the star-studded Gucci Love Parade fashion show in Hollywood.
As far back as June 8, Olivia was seen wearing the cross pendant in an Instastory.
JULY 5, 2021: Harry and Olivia photographed passionately kissing
Harry Styles and Olivia Wilde packed on the PDA, sharing a passionate kiss and couldn’t keep their hands off of each other while in Tuscany in July 2021
The singer and actress were pictured packing on the PDA onboard a yacht in Tuscany, the two who appear to not let their age difference bother them, couldn’t keep their hands off each other as they enjoyed a passionate kiss on the luxury yacht.
The couple enjoyed each other’s company while laying on the yacht before diving into the ocean, the two were said to have had an ‘awesome time’ and it made for the perfect spot for the couple to grow even closer.
April 14, 2021: Harry and Olivia share a romantic night out in London
Olivia Wilde enjoyed a romantic night out with boyfriend Harry Styles at pub in London and the two were said to have to been ‘completely smitten’ with each other
Harry and Olivia were seen enjoying a romantic date night on April 14 2021 at a pub west London. According to others at the pub the couple looked ‘completely smitten’ and were all over each other throughout the night.
Onlookers saw the American actress Olivia, who started dating the former One Direction star after casting him in new film Don’t Worry Darling, stroking his leg beneath their table throughout the evening.
January 4, 2021: Olivia seen arriving at Harry Styles’s LA home
Olivia was pictured arriving back at Harry’s LA home on Monday after ‘growing close’ on the set of their new movie Don’t Worry Darling in January 2021
After ‘growing close’ to each other on the set of Don’t Worry Darling, the Hollywood actress was pictured arriving at the former One Direction heartthrob’s LA home with her luggage in hand and the two were seen driving around California together.
Olivia was spotted arriving at Harry’s LA home just days after the two were spotted holding hands at Harry’s agent’s wedding at the San Ysidro Ranch in Montecito, California.
November 13, 2020: Olivia and Jason Sudeikis split
In November, it was revealed that Wilde and her longtime partner Jason Sudeikis had ended their engagement, after almost a decade together; pictured together in March 2019
The couple who had been together for over a decade and share two children together, son Otis, eight, and daughter Daisy, five, shocked fans when they revealed the news of their breakup.
Although it didn’t seem to take the actress too long to get over her broken heart, as she was seen with boyfriend Harry, who is ten years younger than her, just two months following the split from her love of over a decade.
September 11, 2020: Harry joins Olivia on set of Don’t Worry Darling
Harry Styles replaced Shia Lebouf as the star of Don’t Worry Darling in Olivia Wilde’ film and the sparked a connection and Olivia Wilde ‘enjoyed a romantic night out in west London’ on Wednesday evening according to onlookers (pictured on the set of their new movie Don’t Worry Darling)
On September 11 of 2020 Harry reportedly joined Olivia and sparked their connection when he was cast as actress Florence Pugh’s husband and replaced Shia Lebouf in film Don’t Worry Darling.
The singer who made his acting debut in 2017 film Dunkirk, and signed onto Olivia’s film after impressing both director Olivia and star Florence Pugh when Lebouf was fired for his ‘poor behavior.’
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