Harry Styles and Olivia Wilde’s Relationship Timeline, Explained

Harry Styles and Olivia Wilde made a lot of headlines during their relationship from January of 2021 to November of 2022, and it is still having ripple effects on pop culture today. With the increasing hindsight of clarity, we can began to organize the reports on this romance as well as the public responses. Read on for a full timeline.

It’s worth noting that right now, both Wilde and Style are single as far as we know. Wilde has been single since their breakup, while Styles dated Canadian actress Taylor Russell for a little less than a year after the breakup. Of course, one of the central talking points about this celebrity romance was the 10-year age gap between them, and that seems to be one of the reasons why it is still discussed and referenced today. Read on for the timeline and all the confirmed details on this relationship.

History

For starters, let’s summarize the romantic history of both of these stars for context. Wilde married italian filmmaker Don Tao dei Principi Ruspoli in 2003 when she was 19 years old. They divorced in 2011. Shortly after that, Wilde began dating SNL alum Jason Sudeikis. They got engaged in January of 2013 and had a son in 2014 followed by a daughter in 2016. Their breakup is generally dated to November of 2020, though it still isn’t entirely clear when they broke up.

Styles, meanwhile, had all eyes on him as a teen heartthrob, and raised eyebrows with his first public relationship in November of 2011. He dated English TV presenter Caroline Fleck, who is 14 years older than him, but only for about three months. Styles had another short fling with Taylor Swift in 2012, followed by a longer relationship with Kendall Jenner from 2013 to 2016. Styles then dated model Camille Rowe from 2017 to 2016.

September 2020

From there, we can start Styles and Wildes’ timeline in September of 2020, when Styles was officially cast in Wilde’s movie Don’t Worry Darling. It was Wilde’s directorial debut and was only Styles’ third outing as a film actor. He replaced Shia Labeouf, whom the studio said was removed from the cast due to scheduling issues but was rumored to have had clashes with co-star Florence Pugh, among others on set.

November 2020

Two months later, PEOPLE reported that Sudeikis and Wilde had broken up. A source close to them said that they were still co-parenting amicably and their children were their main priority. That insider also said that they had broken up earlier in the year, but an exact timeframe was not identified.

January 2021

Early in 2021, reports of Styles and Wilde’s relationship first emerged, and it seemed like they had gone public on purpose. They were spotted together at Styles’ agent’s wedding, and they made no effort to hide their PDA. The first hints of scandal came into the story here, as the insider said that things had “quickly turned romantic” between Wilde and Styles after they met, leading some to wonder where this fit in the timeline of Wilde’s separation from Sudeikis.

February 2021

February of 2021 was a busy time for Wilde and Styles, who made their affection for each other clear for all to see. Wilde made a social media post gushing about Styles, reiterating quotes from an interview with Vogue back in December. They were also photographed together several times, and even took a trip to England together where Wilde stayed in Styles’ home.

July – November 2021

Wilde and styles laid low for a few months, but any obvious connection between them generated headlines. In July, paparazzi photographed them kissing on a yacht and sunbathing together. In September, Wilde attended one of Styles’ concerts in Las Vegas, dancing in the front row. In November, Wilde re-posted a promotion for Styles’ new beauty product, and was later spotted wearing one of Styles’ tour t-shirts while grabbing coffee in Los Angeles.

December 2021

Over the course of the year, speculation about Wilde and Styles ran rampant online, and they mostly ignored it. However, in December Wilde sat down with Vogue again, and she addressed fans’ interest in her relationship. She said: “It’s obviously really tempting to correct a false narrative. I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love. I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that.”

That same month, a source told PEOPLE that Styles was getting to know Wilde’s children, while Wilde was getting to know Styles’ mother. They said: “She always seems focused on just making it all work. She is really Harry’s biggest fan.”

April 2022

Styles released his first new song in over two years that spring – “As It Was.” Fans were quick to assume that it was about Wilde, thanks mostly to the line: “I don’t wanna talk about the way that it was, leave America, two kids follow her, I don’t wanna talk about who’s doin’ it first.”

However, the bigger story that month was less joyful. Wilde spoke at CinemaCon, giving a presention on Don’t Worry Darling when someone approached her on the stage. She was served legal papers pertaining to her custody battle with Sudeikis right in the middle of her presentation, making for an easy viral moment.

August 2022

With the press tour for Don’t Worry Darling heating up, Wilde and Styles both found themselves in more interviews than ever. Fans noted that, while Wilde spoke openly about Styles, he avoided mentioning her by name or directly discussing his love life at all. In an interview with Rolling Stone, Styles also discussed the growing controversy about “queer-baiting,” saying: “Sometimes people say, ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone.”

Meanwhile, Wilde told Variety that she did not want to discuss her relationship with Styles in their interview because they were both trying to “protect” it. However, she did allude to the growing commentary from fans about her separation from Sudeikis, saying: “When people see me not with my kids, it’s always ‘How dare she.’ I’ve never seen anyone say that about a guy. And if he is with his kid, he’s a f-ing hero.”

September 2022

The premiere of Don’t Worry Darling at the Venice Film Festival remains one of the most confusing moments in pop culture of the last decade. Styles and Wilde did not sit or stand next to each other during cast photos or during the movie, instead sitting on either side of actor Chris Pine. One clip took over social media, which was bizarre given out mundane and inconclusive it seemed to be. It showed Styles moving his lips and then Pine looking down and giggling, and many commenters seemed to agree that Styles had just spit on his co-star, for some reason. This conspiracy theory has never really been explained.

Later that month, Wilde spoke more directly about their relationship in an interview with Vanity Fair. She said: “The complete horses- idea that I left Jason for Harry is completely inaccurate. Our relationship was over long before I met Harry.” She also praised Styles’ fans for welcoming her and treating her well. Wilde attended Styles’ sold-out show in New York City toward the end of the month, and was seen kissing him afterward.

October 2022

A former nanny for Wilde and Sudeikis spoke to reporters from The Daily Mail in October, claiming that she had seen the breakdown of their relationship firsthand. She said that Sudeikis had first learned about Wilde and Styles by going through Wilde’s Apple Watch. He had allegedly gone so far as to lie down in the driveay in front of Wilde’s car in order to block her from leaving the house to go see Styles. She also said that Sudeikis had hit a breaking point when he saw Wilde preparing a salad for Styles with her “special dressing.”

Sudeikis and Wilde issued a joint statement denying the report, calling all of her statements “false and scurrilous.” In spite of all that, a source close to Wilde said that she and Styles were “thriving” at the time.

November 2022

The very next month, sources told PEOPLE that Wilde and Styles were “taking a break” from their relationship. They said that the decision was mutual and amicable, as their work and responsibilities were pulling them in opposite directions. However, one insider said that the breakup was difficult on Wilde.

“They have had some issues, but Olivia thought they were gonna work through it all,” they said. “She is disappointed. It’s just a tricky situation, though.”

2023

In the months after their breakup, many other reports reiterated that Styles and Wilde were on good terms, but were just “friends” after November. However, their romance made headlines one more time in July when Styles was photographed in some very short swim trunks, revealing a tattoo of the name “Olivia” in large cursive letters on this thigh. Fans speculated that this might be a tribute to Wilde, but he never responded to the commentary.

Wilde and Styles appear to be finished at the time of this writing. Don’t Worry Darling is streaming now on Paramount+.