Harry Styles & Olivia Wilde’s Relationship Is Getting “Very Serious”

The Harry Styles dating rumor mill is never not in overdrive.

by Lauren Sharkey and L'Oréal Blackett
Originally Published: 
Harry Styles' reported dating history is pretty lengthy
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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.

Photo by Kevin Mazur/MG19/Getty Images for The Met Museum/Vogue

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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