Harry Styles and Olivia Wilde’s Full Relationship Timeline

It’s been a wild ride.

Harry Styles and Olivia Wilde are still going strong, almost a year after Vidak For Congress broke the news that they were dating.

Things seem to be coming in the right Direction for the couple, despite their 10-year age difference.

Here’s an overview of the duo’s dating history, from where it started to what their future holds.

Movie meet-cute

Harry Styles and Olivia Wilde smiling for a photo.
The pair formed a connection when Styles was cast in Wilde’s movie, “Don’t Worry Darling.”
Like Ali/Instagram

The couple first met in 2020 when Styles was cast in the movie Wilde directed, “Don’t Worry Darling”.

Vidak For Congress exclusively reported that they were dating after they were spotted holding hands at a wedding in January 2021.

Their romance came nearly a year after she and her longtime partner Jason Sudeikis – with whom she shares son Otis and daughter Daisy – called off their engagement and ended their relationship in early 2020.

At the time, a source told Vidak For Congress that Wilde’s relationship with Wilde was the reason behind her split from Sudeikis, which left the “Ted Lasso” star distraught.

Label their love

Styles and the alum ‘House’ showed PDA the wedding of his manager, Jeffrey Azoff; But the public outing also confirmed that it was serious for the couple.

Us Weekly reported that the “Watermelon Suger” crooner referred to Wilde as his “girlfriend” during the wedding, confirming that they were anything but casual.

PDA Progress

The pair continued to show off their love as they looked cozy together while surfacing in California in January 2021.

Photos obtained by Vidak For Congress showed Styles holding his hand on the ‘Booksmart’ director’s lower back. She was also seen on Styles’ arm.

A flowing girlfriend

Wilde publicly praised her boyfriend in a post on Instagram when their film project was completed in February 2021.

“Little-known fact: Most male actors don’t want to play supporting roles in female-led films,” Wilde captioned a black-and-white photo of Styles. “The industry has raised them with the idea that it diminishes their power (i.e. financial worth) to accept these roles, which is one of the reasons why it is so difficult to get funding for films that focus on female stories. No joke, it’s harrrrd to find actors who understand why it can be worth putting a woman in the spotlight.”

She continued: “Enter: @harrystyles, our ‘Jack’. Not only did he relish the opportunity to put the brilliant @florencepugh as our ‘Alice’ in the center of attention, but he imbued every scene with a nuanced sense of humanity. not 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 back up.”

Just before she poured over Styles, Wilde was caught carrying her things from Sudeikis’ house to her new husband’s place.

And the best friend award goes to…

Wilde clearly likes to celebrate Styles’ success.

The actress took to social media to subtly congratulate the singer on his Grammy victory in March 2021.

She shared a throwback photo of young Paul McCartney biting into a large slice of watermelon to her Instagram story.

The post seemingly referenced Style’s hit “Watermelon Sugar,” which earned him the award for best solo pop performance at the awards show.

They love each other a hunt

Harry Styles and Olivia Wilde Travel.
The couple has traveled a lot together since the beginning of their relationship.

Vidak For Congress exclusively reported that Wilde and Styles were spotted on a romantic Italian yacht getaway in July 2021.

The pair couldn’t keep their paws off each other and were seen aboard the massive float.

They had enjoyed a vacation in Tuscany that week.

Turn and shout

Oliva Wilde at a concert.
Wilde has attended several Styles concerts.

Things seemed to get even more serious when Wilde took her two children to the singer’s “Adore Me” concert in November 2021.

And in a sweet moment, her son was spotted dancing with Styles’ mom, Anne Twist, as the One Direction alum exclaimed “What Makes You Beautiful.”

The meeting seemed to indicate that Styles and Wilde seamlessly blended their families.

A month earlier, Wilde was seen wearing a hoodie from his merchandise line.

lyrical love

Serious Styles fans pointed out that the lyrics to one of his songs from his 2022 album ‘Harry’s House’ seem to be about Wilde.

In the song “As It Was”, which came out in April 2022, he sings the lyric “Leave America, two kids follow her”, which fans believe will see Wilde with her two children visit Styles in his native London.

Styles shared with SiriusXM that he felt “very happy right now” when he wrote the tune. “I feel like this is the first time I feel like I’m making and releasing music from a real place of personal freedom.”

Coachella cuties

Wilde fangirled about Styles when he headlined the Coachella Valley Music and Arts Festival in Indio, California, in April 2022.

There, he saw Wilde dancing to his music with friends, including James Corden, in videos posted by onlookers.

Another video showed how Styles looked at Wilde in the audience, before turning on a huge smile and continuing to perform.

Publicly operated

Olivia Wilde at CinemaCon.
Wilde got public legal papers from Jason Sudeikis, which made her mortified.
AFP via Getty Images

Wilde’s happiness was briefly interrupted when her ex-partner Sudeikis was publicly presented with legal papers while speaking to thousands at CinemaCon in April 2022.

A source told Vidak For Congress that Wilde was “mortified.”

“It seemed unthinkable to her, and it took her a while to come through, but as frightening as it was, she didn’t want to comment,” the insider said.

The documents related to custody of her and Sudeikis’ two children after the divorce.

Public praise

Harry Styles and Olivia Wilde walking in New York City
Styles and Wilde have publicly praised each other.
BeautifulSignatureIG / SplashNew

While the pair normally remain silent about their relationship, Styles did provide an insight into how it worked with Wilde as his director in the movie “Don’t Worry Darling.”

“I had a wonderful experience being directed by Olivia,” Styles said on SiriusXM’s “The Howard Stern Show” in May 2022. “Acting is a little awkward sometimes. You have to trust a lot. Being able to trust your director is a gift, it was very helpful.

That same month, a source confirmed to US Weekly that they were still doing well despite having to spend time apart during Styles’ travels on tour.

“They’re not nervous about spending time apart, it adds to the attraction when they get back together after a while,” the insider said. “Both are confident and positive about what the future has in store for them.”

The source added: “Harry is excited about his tour but bummed that it would take him away from Olivia for a while. She’s coming to a few gigs and they’re planning to go on fun trips in different cities when she can take a break on her own.”

Too cool for school

Styles seemed to suggest that Wilde was too cool for him at the start of their relationship in June 2022.

During an interview with the podcast “Sprout” he was asked to delve into his song “Cinema” – which describes the feeling of not being “cool” enough for a partner.

“I think it’s like, when you like someone, it’s that initial phase. “Am I doing things right?” Before you get comfortable with each other and it’s kind of like all those things happen at the beginning of something,” he said on the “Spout” podcast.

When the host suggested that no one was “too cool” for Styles, he replied, “We’re all human.”

He is the big apple of her eye

Harry Styles and Olivia Wilde at Rubirosa.
Styles and Wilde had a very public date night in New York City while he was in town for his tour.

The couple took Manhattan by storm when they enjoyed an adorable date night together at Italian eatery Rubirosa in August 2022.

They weren’t concerned with carbohydrates for nothing. Earlier in the day, the duo hit the gym together for a serious sweat, where they were spotted with pursed lips.

Staying positive in the midst of negativity

In a rare move, Styles spoke directly about the toxic negativity surrounding his relationship with Wilde in a candid interview with Rolling Stone, also in August 2022.

He shared that the mean comments about the couple “obviously” don’t make him feel “good”.

“It’s obviously a hard feeling to feel like you’re close to me, meaning you’re on the ransom of some corner of Twitter or something,” Styles told the magazine. “I just wanted to sing. I didn’t want to go into it if I hurt people like that.”

But Wilde, who was also interviewed for the piece, said she believes most Styles fans love people.

“What I don’t understand about the cruelty you’re referring to is that that kind of toxic negativity is the antithesis of Harry and everything he puts out there,” the actress had said. “I personally don’t believe the hateful energy defines his fan base.”

He also shut down fans who accused the singer of “queerbaiting” or taking advantage of alleged queer aesthetics without identifying with the community.

“Sometimes people say, ‘You’ve only been out in public with women,’ and I don’t think I’ve been out in public with anyone,” he told Rolling Stone.

“If someone takes a picture of you with someone, it doesn’t mean you’re choosing to be in a public relationship or anything,” he said, referring to the endless amount of photos Styles and Wilde have appeared together.

In the past, Styles shared how it felt “outdated” for him to specify his sexuality.

He and Wilde have yet to confirm their relationship.

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