Who is Harry Styles dating? A peek inside the 'Watermelon Sugar' singer's love life

We're always wondering, 'Who is Harry Styles dating?' Well, it looks like things are heating up between Harry and this A-list actress

Harry Styles attends The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City.
(Image credit: Dia Dipasupil/FilmMagic/Getty Images)

The One Direction star is one romantically busy dude, so we're often left wondering: Who is Harry Styles dating? 

The "Sign of the Times" singer has been linked to many a famous model and actress over the years, but his latest romance is causing fans to collectively swoon...and simultaneously begrudge his new flame. (Some 1D admirers can't help but feel a smidge jealous, and we can't blame them.) 

We'll give you the scoop on the "Watermelon Sugar" crooner's love life, both present and past.

Who is Harry Styles dating right now?

Rumors of Harry Styles and Olivia Wilde's relationship first began blossoming at the beginning of 2021 when the two attended his agent's wedding together...in matching Gucci ensembles. 

The Grammy award-winning singer will appear alongside actors Florence Pugh and Chris Pine in Wilde's new film, Don't Worry, Darling—and his performance garnered praise from the actress-director via Instagram.

Wilde took to social media to capture the film's strong points as wrapping came to a close in February 2021, one of which being Styles' ability to let the women of the cast shine.

"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," Wilde wrote alongside a long list of other compliments.

Check out her sweet Instagram shout-out for yourself! Seems pretty generous, wouldn't you say?

Harry Styles and Olivia Wilde yacht pics

Fast forward to summer 2021: Harry Styles and Olivia Wilde were spotted engaging in some major PDA in Monte Argentario, Italy, on a relaxing vacation ahead of their new work projects.

Judging from the sexy swim sessions and smooches while aboard a yacht, per Page Six, it would be safe to say that the lovebirds are indulging in some serious amore while abroad.

Harry and Olivia's relationship timeline

Although still fairly new, the romance between Harry Styles and Olivia Wilde has been going strong since the start of 2021, following Wilde's divorce from actor Jason Sudeikis in late 2020. 

However, they're both relatively quiet and attempt to stay out of the spotlight. She reveals hints of their closeness on social (including several behind-the-scenes Don't Worry, Darling snapshots), but it's glimpses of them while out on vacation (like while in the UK in May 2021) that most pique fans' interests. 

A source confirmed to US Weekly that the two hit it off immediately while on set, saying that Styles brings out Wilde's silly side. Seems like a good recipe for romance between the two celebs!

How old is Olivia Wilde compared to Harry Styles?

Born on March 10, 1984, Olivia Wilde is currently 37 years old. That makes her a decade older than her boyfriend Harry, who was born on February 1, 1994. Her ex, Jason Sudeikis—with whom the actress was with since 2011 and shares two children, son Otis and daughter Daisy—is 45 years old. 

What is Harry Styles' dating history?

1. Harry Styles and Taylor Swift

We all knew Harry was trouble when he walked in. Taylor Swift had no qualms about dedicating a few heartbreak anthems to her 2013 relationship with the former boy bander, including her 2015 single entitled—duh—"Style."

2. Harry Styles and Nicole Scherzinger

Harry appears to gravitate towards older women, and Nicole Sherzinger is one of them. They reportedly dated while he was 19 years old and she was 35 in 2013, having first met when the Pussycat Dolls singer was a judge on X-Factor while Styles was competing with the rest of One Direction back in 2010.

He was also previously linked to Erin Foster, Tess Ward, and Caroline Flack, all of whom were older.

3. Harry Styles and Kendall Jenner

The singer and supermodel Kendall Jenner were linked on several occasions, even having their own PDA-filled, paparazzi-snapped yacht sail back in 2015, but it seems that now the two are just close friends.

4. Harry Styles and Sara Sampaio

Styles was linked to the Victoria's Secret model—as well as her counterpart Georgia Fowler—in 2015, per Page Six.

5. Harry Styles and Camille Rowe

Reportedly introduced by mutual friend Alexa Chung, Styles and French model Camille Rowe dated for about a year, from summer 2017 to July 2018. 

Several songs on Styles' sophomore album, Fine Line, are rumored to be about his relationship with Rowe and their subsequent breakup, including tracks "Falling" and "Watermelon Sugar."

The song "Cherry" even samples a voicemail Rowe left for Styles when they were together. In it, she says, "Coucou! Tu dors? Oh, j’suis désolée / Bah non, nan, c’est pas important / Bon allez … on a été à la plage, et maintenant on … / Parfait!" which translates to "Hey! Are you asleep? Oh, I’m sorry / Well no, nope, it’s not important / Alright … we went to the beach and now we … / Perfect!"

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Is Harry Styles bisexual?

Much has been made of the androgynous star's sexuality over the years, with many questioning if Styles identifies as bisexual, pansexual, or queer. An infamous and long-running rumor about the singer is that he engaged in a romantic relationship with fellow One Direction bandmate Louis Tomlinson while they were part of the group, resulting in the ship "Larry Stylinson," however, both parties have debunked that as mere fan fantasy.

When asked about his much-scrutinized sexuality in a 2019 interview with The Guardian, Styles said this: "It's not like I'm sitting on an answer, and protecting it, and holding it back. It's not a case of: 'I'm not telling you 'cause I don't want to tell you.' It's not: 'Ooh, this is mine and it's not yours.' It's: 'Who cares?' Does that make sense? It's just: 'Who cares?'"

"I think it’s a very free, and freeing, time. I think people are asking, ‘Why not?’ a lot more. Which excites me," said the singer, "It’s not just clothes where lines have been blurred, it’s going across so many things. I think you can relate it to music, and how genres are blurring…"

Regarding his oft-flamboyant, gender-bending wardrobe, Styles told The Guardian: "What women wear. What men wear. For me it’s not a question of that. If I see a nice shirt and get told, ‘But it’s for ladies.’ I think: ‘Okaaaay? Doesn’t make me want to wear it less though.’ I think the moment you feel more comfortable with yourself, it all becomes a lot easier."

When the question of queer-baiting—teasing queer subtext as a mere marketing ploy—arose, Styles shot it down, replying: "Am I sprinkling in nuggets of sexual ambiguity to try and be more interesting? No...In terms of how I wanna dress, and what the album sleeve’s gonna be, I tend to make decisions in terms of collaborators I want to work with. I want things to look a certain way. Not because it makes me look gay, or it makes me look straight, or it makes me look bisexual, but because I think it looks cool. And more than that, I dunno, I just think sexuality’s something that’s fun. Honestly? I can’t say I’ve given it any more thought than that."