Harry Styles & Olivia Wilde’s Relationship Is Getting "Very Serious" (2024)

In 2021, Harry Styles has produced a video with Phoebe Waller-Bridge, teased that he’s releasing new music, and is set to open the 2021 Grammy Awards on Sunday, March 14. Styles’ musical performance won’t be his only opportunity to be recognized at the awards show. He’s also nominated for three trophies — best pop solo performance for “Watermelon Sugar,” best pop vocal album for Fine Line, and best music video for “Adore You.” Naturally, Styles has also proven that even in lockdown, he can serve some serious looks. His dating life is also one of the biggest reasons you might spot his name in recent headlines. Since inquiring minds want to know who Harry Styles is dating, it’s time to find out.

The singer-songwriter has had a series of girlfriends over the last few years, including a Kardashian and Victoria’s Secret model. After a period of being single, it seems he’s now loved-up with a Hollywood A-lister. Turns out finding love in lockdown is possible. If you’re Harry Styles, that is. It’s been reported that the “Watermelon Sugar” singer is dating actor and director Olivia Wilde. The pair recently finished working on Wilde’s latest film together, Don’t Worry Darling.

Rumors about a Styles and Wilde love affair started to surface in January 2021. In November 2020, Wilde’s seven-year engagement to Jason Sudeikis came to an “amicable” end. In the new year, Styles and Wilde were seen holding hands together at a wedding. A source told People, “They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks.”

Similarly, Entertainment Tonight reported that the pair had met on set and built a connection. ET also said they “wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.” Skip to February 2021 and People have a source saying that the two "seem very serious.” They’re filming together and "spend all their time together." They also said that Wilde is "very happy.” The pair have been pretty private on their social media pages but all signs suggest that, as I’ve been doing face masks and counting down the days to the end of lockdown, love has been blossoming on the Don’t Worry Darling set.

Styles has always kept his dating life pretty private. The “Adore You” singer has rocketed to superstar status, so it’s understandable he’d keep some things to himself. He never officially announced he was single last year. However, in March 2020, he did express hopes of “dating normally.” During an interview, he told Howard Stern: "It's always kind of a balance thing because you want to date normally, but then you also want to protect it so it can be normal."

Normal doesn’t seem likely for the hit-maker. Some even tried to start a dating rumor when Styles and Adele were spotted on holiday together at the start of 2020, notes Cosmopolitan, but most were simply excited at the thought of a musical collaboration.

Styles has been romantically linked to a series of famous people. Serious fans will remember his fleeting, rumored relationship with Kendall Jenner. They were first pictured together in 2013 when he was still part of One Direction. However, it was reported they broke things off shortly afterward. They’ve been seen together since but it seems things are purely platonic between the pair.

It was reported that Styles was in a relationship with Victoria's Secret model Camille Rowe in 2017. However, according to The Sun, the pair split in 2018. Just as his dating history has been analyzed so have his lyrics. It is widely believed that Styles' track, "Cherry", is about the 31-year-old. As The Cut states, the line “Does he take you walking ’round his parents’ gallery?” could reference the fact Rowe is now dating a gallery owner. Plus, the end of the song includes a voicemail from her.

Styles' relationship history may have left you wondering; does he ever date non-famous people? If you’ve got a lot of love for the “Fine Line” singer you're in luck. "I do," he recently told the Guardian. "I have a private life. You just don’t know about it.” Mysterious as always.

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Harry Styles & Olivia Wilde’s Relationship Is Getting "Very Serious" (2024)

FAQs

Who was Harry Styles longest relationship? ›

Who has Harry Styles dated the longest? To date, Styles' longest relationship has been with Wilde. The pair dated for nearly two years.

Who is Harry Styles first love? ›

Felicity Skinner

Styles' first-ever girlfriend at age 15, Felicity, opened up about him after he got famous. "He was really sweet. He was a really good boyfriend, very romantic and, yes, shy," she said of the relationship, which lasted a little under a year.

Why did Jason and Olivia split? ›

Wilde said she made the decision to end her relationship with Sudeikis because she had grown and changed during their time together. "I evolved a lot between when I was 27 and 35. I found myself as a director. And I think I found myself as an individual.

Who has Harry Styles had a crush on? ›

A video of Harry Styles saying Emily Ratajkowski was his "celebrity crush" has resurfaced online. In a 2014 interview, Styles was asked for his celebrity crush and named the "Gone Girl" star.

Did Olivia cheat on Jason with Harry? ›

Well, the 38-year-old director is finally setting the record straight: there was no overlap between Sudeikis and Styles — and she had some choice words to emphasize her disgust at the rumor. “The complete horses**t idea that I left Jason for Harry is completely inaccurate,” she explained to Vanity Fair.

Who is Olivia Wilde married to now? ›

Image of Who is Olivia Wilde married to now?
Don Tao dei Principi Ruspoli is a Thai born Italian-American filmmaker, photographer, musician, and co-founder of The Bombay Beach Biennale. He is the son of Alessandro Ruspoli, 9th Prince of Cerveteri and part of the Papal nobility.
Wikipedia

What did Jason do to Olivia Wilde? ›

Wilde was served in 'most aggressive manner'

"Jason's actions were clearly intended to threaten me and catch me off guard," Wilde reportedly said in the new documents. "He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible."

How long was Harry Styles with Camille Rowe? ›

' Rowe and Styles started dating mid-2017 before ending their relationship a year later.

How long was Harry and Camille together? ›

Styles and Camille Rowe dated for a full year before parting ways. They originally met through a mutual friend.

Who did Harry Styles date immediately after Taylor Swift? ›

Harry's next romance after Taylor was rumored to be Kimberly Stewart, a British socialite, model and actress. She starred in a few television and film projects, including episodes of Pacific Blue and Going to California and the movie Black and White, which starred Jared Leto and Robert Downey Jr.

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