From coworkers to friends and more! Fans were taken aback by Olivia Wilde and Harry Styles’ fast courtship, which began when they met on the set of Don’t Worry Darling.

Harry Styles & Olivia Wilde Relationship Timeline: Are They Dating?

In January 2021, the couple made headlines when they were caught holding hands at Styles’ manager’s wedding. When the twosome started working together, a source told Us Weekly exclusively that they formed a relationship.

“Onset, Harry and Olivia had a nearly instant connection,” the insider claimed. “It was only a matter of time before they started dating.”

Wilde began dating Styles two months after she divorced her fiancé Jason Sudeikis and three months after Styles joined her project. Sudeikis and the Booksmart director have two children: son Otis and daughter Daisy, who have been together for almost a decade.

When the connection was first reported, a source informed Us that Styles was not the reason for the House alum’s breakup with Ted Lasso.

“Harry did not end a relationship,” the person claimed.

Despite the fact that Styles did not come between Wilde and Sudeikis, the new pair initially tried to keep their relationship private on set.

Olivia Wilde & Harry Styles's Relationship Timeline | Glamour UK

In January 2021, an insider told Us, “Olivia and Harry were able to keep their relationship under wraps for a bit until it became public knowledge.” “They were quite cautious and even sleuthy about it at times, but the tiny number of people who worked with them every day eventually found it out.”

Florence Pugh, Chris Pine, Gemma Chan, KiKi Layne, and Nick Kroll feature in the psychological thriller, which is set in the 1950s and centered around a housewife.

Wilde visited Styles in London after production concluded in February 2021, where they enjoyed some alone time.

In April 2021, an insider told Us, “People in London tend to respect people’s privacy, so they probably feel comfortable strolling around by themselves and don’t feel like they need a bodyguard.”

During their London vacation, the couple was “seen in local bars.”

“They were walking close together and their arms were linked together,” said an insider who ran across the couple on one of their casual strolls. “They appeared to be quite close and cuddling with each other.”

The couple’s affair grew hotter as the actress from Life Itself openly supported her beau’s music and film talents. She “clearly” watched his Eternals performance, which she mentioned on Instagram, and even danced at numerous “Love on Tour” concerts with her kids and his mother, Anne.

“Olivia was nonstop dancing on the floor at Harry’s gig at Madison Square Garden,” an eyewitness told Us exclusively about Wilde’s appearance at the musician’s tour stop in New York City in October 2021.

Relive Styles and Wilde’s surprise romance by scrolling down:

In September 2020, Styles was cast as Pugh’s spouse in Don’t Worry Darling. Shia LaBeouf, who was sacked from the part by Wilde after reportedly clashing with the cast and crew, was replaced by the singer.

January 2021
When they visited Styles’ manager Jeffrey Azoff’s wedding in California, the two were seen holding hands.

During his wedding speech, the former One Direction member even referred to Wilde as his “girlfriend,” according to a source.

January 2021
After making their romance public, the two were seen returning to Styles’ house in Los Angeles.

January 2021 During a stroll in Santa Barbara, California, Styles, and Wilde continued to flaunt their new affair. As they walked side by side in January 2021, photos showed the actor reaching out to caress Wilde’s waist.

2021 February
As production on Don’t Worry Darling came to a close, the New York native resorted to social media to thank her cast.

In February 2021, Wilde remarked on Instagram, “Little known fact: most male actors don’t want to accept supporting roles in female-led films.” “Accepting these parts reduces their power (i.e. financial value) in the eyes of the industry, which is one of the reasons it’s so difficult to acquire funding for films with female protagonists. It’s impossible to find actors who understand why it could be worthwhile to give a woman the spotlight.”

She went on: “Enter our ‘Jack,’ @harrystyles. He not only relished the chance to let the great @florencepugh take center stage as our ‘Alice,’ but he also instilled a subtle sense of compassion into every moment. He didn’t have to join our circus, but he did so with elegance and humility, and he continues to amaze us with his talent, warmth, and ability to drive backward.”

In a cast photo, the couple also posed close to each other.

March 2021
After her beau won Best Pop Solo Performance at the Grammys in 2021, the director celebrated him quietly.

Wilde shared a Polaroid snapshot of Paul McCartney chomping down on a watermelon slice, alluding to Styles’ song “Watermelon Sugar.” With a raised-hand emoji, Wilde captioned the Instagram photo.

April 2021
A source told Us exclusively, “Harry and Olivia have been spending time in London.” “She’s been staying with him. They’re attempting to maintain a low profile by visiting sites that aren’t overly crowded.”

Styles was cast in My Policeman alongside Emma Corrin in May 2021, and PDA-filled set photos threw fans into a frenzy. However, a source told Us that Wilde was unconcerned.

July 2021
“After the couple was pictured packing on the PDA on vacation in Italy, an insider exclusively told Us, “Olivia is genuinely smitten by Harry.” “He brings her much joy.” He seems to have brought out her exuberant side. The fact that they don’t hide their relationship from the public is something that works for them. They are unconcerned about who is observing them pack their PDA.”

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July 2021
Olivia and Harry have an easiness to their relationship; they love and support one other, but they also let each other be free and work on their own,” a source told Us.

During their respective professional undertakings, Wilde and Styles have been in “continuous communication,” according to the insider.

2021 December
On December 5, the filmmaker was seen conducting errands in Los Angeles wearing a black hoodie from Styles’ cosmetic company. The “Pleasing” emblem was emblazoned over the breast of the hoodie.

January 2022
After Styles’ Eternals costar Gemma Chan shared behind-the-scenes photos of herself and the singer in their MCU superhero costumes, Wilde replied on Instagram, “Watching now obviously.”

April 2022
After Styles released “As It Was,” the first single from his third album, fans immediately began poring over the lyrics for hints. Some listeners thought the line “Leave America, two kids follow her” was a reference to Otis and Daisy, and that the bridge hinted at his infatuation with Wilde.

Styles gushed to SiriusXM’s The Morning Mash Up about the song’s origin, saying that he felt “very joyful at the moment,” which influenced his songwriting. “It’s the first time I feel like I’m writing music and putting songs out from a real point of personal independence,” he remarked.

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May 2022
The duo was pictured wandering across Italy ahead of the release of Harry’s House, Styles’ third album. “Olivia and Harry enjoy coming to Italy together,” a source told Us about the couple’s trip. “It’s where they go to relax and reconnect as a couple. They adore the food, the people, the architecture, and everything else about it. They are looking forward to spending some time together before he returns on tour.”

May 2022
During an appearance on SiriusXM’s The Howard Stern Show, Styles said, “I had a lovely time being directed by Olivia.” “Acting might be a little unsettling at times. A lot of confidence is required. It was quite beneficial to be able to trust your director.

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