Harry Styles and Olivia Wilde’s complete relationship timeline

Wilde publicly praised her boyfriend in a post to Instagram when their film project wrapped in February 2021.

“Little known fact: most male actors don’t want to play supporting roles in female-led films,” Wilde wrote along a black-and-white photo of Styles. “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.” 

She continued, “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.”

Right before gushing over Styles, Wilde was snapped moving her things out of Sudeikis’ home and into her new man’s place.

And the award for Best Boyfriend goes to…

Wilde clearly likes to celebrate Styles’ success.

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

She shared a throwback pic of young Paul McCartney biting into a big slice of watermelon to her Instagram Story.

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

They like each other a yacht

Page Six exclusively reported that Wilde and Styles were spotted enjoying a romantic Italian getaway on a yacht in July 2021.

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

They had been enjoying a vacation in Tuscany that week.

Twist and shout

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

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

The gathering seemed to indicate that Styles and Wilde were seamlessly blending their families.

A month prior, Wilde was seen wearing a hoodie from his merch line.

Lyrical love

Serious fans of Styles 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 dropped in April 2022, he sings the lyrics, “Leave America, two kids follow her,” which fans believe is about Wilde with her two kids coming to visit Styles in his native London.

Styles shared with SiriusXM that he felt “really happy at the moment” when writing the tune. “I feel like it’s the first time I feel like I’m kind of making music and putting music out from a real place of kind of personal freedom.”

Coachella cuties

Wilde fangirled over Styles as he headlined the Coachella Valley Music and Arts Festival in Indio, Calif., in April 2022.

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

Another video showed Styles spotting Wilde in the crowd before he gives a big smile and continues on performing.

Publicly served

Wilde’s happiness was briefly halted when she was publicly served legal papers from her ex-partner Sudeikis while she was giving a speech to thousands of people at CinemaCon in April 2022.

A source told Page Six that Wilde was “mortified.”

“It seemed unthinkable to her, and it took a moment to set in, but as mortifying as it was, she did not want to give a reaction,” the insider said.

The documents concerned the custody of her and Sudeikis’ two children following the separation.

Public praising

Though the pair typically stay mum about their relationship, Styles did give insight into how it was working with Wilde as his director in the film “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 kind of uncomfortable at times. You have to trust a lot. Being able to trust your director is a gift, that was very helpful.

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

“They’re not nervous about spending time apart, it adds to the attraction when they reunite after some time off,” the insider said. “Both of them are secure and positive about what the future holds for them.”

The source added, “Harry’s excited about his tour but bummed it’ll take him away from Olivia for a while. She’ll come to a few of the gigs and they’re planning on making fun little trips in various cities when she can take a break herself.”

Too cool for school

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

During an interview with “Sprout” podcast, 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, that initial phase. ‘Am I doing things right?’ Before you get comfortable with each other and it’s kinda, like, all of that stuff happens at the start of something,” he said on the “Spout” podcast.

When the host suggested that nobody was “too cool” for Styles, he responded, “We are all human.”

He’s the Big Apple of her eye

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

They were carbo-loading for a reason. Earlier in the day the duo hit the gym together for a serious sweat where they were spotted locking lips.

Staying positive amid negativity

In a rare move, Styles directly addressed 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 pair “obviously” don’t make him “feel good.”

“It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something,” Styles told the mag. “I just wanted to sing. I didn’t want to get into it if I was going to hurt people like that.” 

But Wilde, who was also interviewed for the piece, shared that she believes most of Styles’ fans are loving people.

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

He also shut down fans who accused the singer of “queerbaiting,” or profiting off perceived queer aesthetics without identifying with the community.

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

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

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

He and Wilde have yet to outright confirm their relationship.