Celebrity Couples
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Harry Styles on the red carpet at the 63rd Annual Grammy Awards, at the...

Harry Styles And Olivia Wilde’s Relationship Timeline Is, Well, Wild

Here’s how the “Golden” couple got their start.

Jay L. Clendenin/Los Angeles Times/Getty Images

Imagine, for a moment, being Olivia Wilde in late 2020. You are successful and brilliant and can rock a deep V like it’s nobody’s business. You’re in charge on movie sets, including for your upcoming project Don’t Worry Darling, set to star Florence Pugh and Harry Styles. And you’re reportedly between two romances with the world’s most charming and delicious men: goofy, sensitive Hot Dad Of The Century, Jason Sudeikis, and adorable, inimitable best-dressed showman, Styles. Life is your candy store and you’re just a happy little kid scooping gummy bears by the fistful.

Today, almost a year after Wilde and Styles were first spotted together in public, everyone is curious about their relationship timeline. The two are reportedly together and better than ever. Their movie is almost done, slated to release in September 2022. Styles has just wrapped his second major concert series, Love On Tour. Wilde is already getting to work on her upcoming role in Damien Chazelle’s Babylon, set in 1920s Hollywood. They’re going for long walks together in the U.K. and taking boat rides in Italy. They’re living their best lives.

But how did we get here? When (and why) did Wilde split from Sudeikis and wind up with someone who in many ways seems to be so totally different — and so soon? For answers to these questions and more, step into the wild world of Harry Styles and Olivia Wilde’s relationship timeline, complete with covert gifts, wedding appearances, and conspicuously coded messages on social media.

September 2020: Harry Styles Is Cast In Don’t Worry Darling

On Sept. 11, 2020, Deadline reported that Styles had been cast to replace Shia LaBeouf in Wilde’s new film, Don’t Worry Darling. Two months later, Wilde was interviewed as part of Styles’ cover profile for Vogue. She told them at the time that she and the film’s costumer, Arianne Phillips, did “a little victory dance” when they’d learned they’d officially signed Harry to the film. “We knew that he has a real appreciation for fashion and style,” she explained. “And this movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that he is so enthusiastic about that element of the process—some actors just don’t care.”

2020: Wilde & Sudeikis End Their Seven-Year Engagement

Fans learned of Wilde and Sudeikis’ split in November 2020, after nearly a decade as a couple and almost as long as fiancés. The two have kids together, 6-year-old Otis Alexander and 4-year-old Daisy Josephine, whom they co-parent and for whom they share custody. At the time of the announcement, People reported that the breakup happened in early 2020 and was “amicable,” though there were varying reports in the coming months about Sudeikis’ state of mind. Some claimed he was “heartbroken” and that he was reportedly holding out for “hope that maybe there's a way for them to repair things.” However, according to Entertainment Tonight, the duo actually parted ways in November.

January 2021: Wilde & Styles Hold Hands At A Wedding

In January 2021, Wilde and Styles were spotted holding hands at Styles’ agent's wedding at the San Ysidro Ranch in Montecito, California. Leaked images from the event sent some shockwaves through their fanbases — in part because Wilde and Sudeikis had only recently publicized their split. When the cozy-looking photos surfaced, some fans wondered if the situation smelled fishy. Some went so far as to wonder if Styles was the reason for the Sudeikis-Wilde split, though it’s now been confirmed several times that this was not the case.

Amid whisperings that the situation was all just a publicity stunt for their upcoming film, Entertainment Tonight reported that the pair had gotten close while filming for Don’t Worry Darling and had built an “organic” relationship together. Twitter promptly mourned the loss of Single Harry Styles.

February - March 2021: They’re “Happy” Together

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In February 2021, a source told People that Wilde is “very happy with Harry” and that the two seemed “very serious.” Also in February, Wilde posted a doting message to Styles, commending him for his work on their film and his willingness to play a supporting role under the female protagonist, which, she said, continues to be rare in Hollywood. “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. 👊 #dontworrydarling." Swoon.

A few weeks later, when Styles won the Grammy for Best Pop Solo Performance for his hit single, "Watermelon Sugar" (his first Grammy win), Wilde posted what fans thought were cryptic images that alluded to her beau. They included a snap of Mick Jagger in an outfit Styles would 100% be wearing today, and a snap of a younger Paul McCartney biting into a watermelon. Suspicious…

April 2021: They Spend A Lot Of Time Together In The U.K.

In April 2021, a source told Entertainment Tonight that the couple was enjoying plenty of “one-on-one time” in the U.K., living the slow life after months of filming in L.A. According to the source, "Their idea of a good time is going for a long walk and ducking into a neighborhood pub.” Um, can I join?

July 2021: They Make Out On A Boat In Italy

In order to receive your official Hot Celebrity Couple badges in the mail, you must first make out on a boat in Italy. It’s the rules. Wilde and Styles passed that test in July, when they were spotted kissing and frolicking and looking generally lovestruck together in southern Tuscany. I will ask again, nicely: Any room for a third, y’all?

September 2021: Wilde Is Supports Harry Styles At Love On Tour

Wilde was spotted supporting Styles at his show in Las Vegas in September 2021, the first stop on his tour. According to eyewitnesses, Wilde was singing along to almost every song. The source added, "She was so happy and dancing all night!"

November 2021: Wilde Appears To Wear Styles’ Jewelry

In November, Wilde was spotted with a gold cross necklace that fans recognized as Styles’ — or at least something very similar. Fans were flabbergasted. TikToks were made comparing the two pieces of jewelry. And fan theories about the reported couple continued to spiral.

December 2021: Wilde Is Happier Than Ever

On Dec. 5, 2021, Vogue published the cover story for their January issue featuring Wilde. The interview was mostly about her storied career, her perspective on Hollywood, and her childhood, though it touched on her current relationships and personal life. When asked about the criticism she’s received for potentially dating someone 10 years younger than she is, Wilde responded tactfully — never confirming her relationship with Styles but alluding to it.

“It’s obviously really tempting to correct a false narrative,” she told Vogue. “But 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.”

Also in the interview, she gushed about her joy. “In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us,” she said. “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.”

If I were reportedly dating Harry Styles, I think I’d feel that way, too.