20 Famous Women Harry Styles Has Dated: Who Is Harry Style’s Current Girlfriend? His Dating History Explored

Harry Styles’ relationship history is extensive: here’s a rundown of all his exes from past relationships before his current girlfriend Emily Ratajkowski.

Whenever there’s a heartthrob currently dominating the silver screen or pop music charts, people are always furiously googling whether or not they’re romantically involved with a significant other. The more popular you are, the less private your private life is. And one of the most beloved stars folks wants to know the dating history of is Harry Styles.


A recent video of Emily Ratajkowski and Harry Styles passionately kissing in Tokyo has sparked dating rumors.

Fans are starting to speculate on social media that singer Harry Styles and actress Emily Ratajkowski are dating.

Emily and Harry were being romantic with each other while they were both recently in Tokyo. According to People, Harry was in the country for his 2023 “Love On Tour,” which had concert dates on both March 24 and March 25.

They were seen together on the March 25. The two celebrities haven’t had any public appearances with each other before. Currently, Emily and Harry haven’t commented on the relationship rumors.

Harry Styles was in an almost 2 years relationship with Olivia Wilde.

The former singer from One Direction who managed to create a successful solo music career and act in high-profile movie projects dated Olivia Wilde, who cast Styles in her psychological thriller Don’t Worry Darling. Rumors about a romance between Wilde and Styles began around the same time filming began in November of 2020, and there’s been a whole bunch of drama surrounding the union of these two stars.

The source of the drama is the fact that Wilde has two children with her former boyfriend, actor Jason Sudeikis. Different outlets have reported varying opinions and reactions to their relationship. Some folks have commented that they found the relationship between Wilde and Styles “scandalous” namely for two reasons. One: there’s a 10-year age gap between the singer and the actress.

Harry Styles and Olivia Wilde in the right bottom corner on the set of #DontWorryDarling recently! pic.twitter.com/TrHGBDkio0— DON’T WORRY DARLING SPOILERS (@DWDspoilers) February 1, 2021

The other reason is the nature and timing of how Wilde and Styles reportedly met one another on the set of her film. Some reports from folks who are allegedly close to Wilde and Sudeikis stated that Jason was completely taken off-guard by Wilde’s relationship with Styles and that the two were reportedly still together while she was seeing Harry.

According to People magazine, Harry, 28, and Olivia, 38, are “taking a break,” citing their busy work schedules for the split.

“He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A.,” a source told the outlet. “It’s a very amicable decision… they’re still very close friends.”

Another source added, “Right now, they have different priorities that are keeping them apart.” Harry has headed abroad for his Love on Tour shows, while Olivia is set to start directing her next film, Perfect, which tells the story of American gymnast Kerri Strug at the 1996 Olympics.

Who else has Harry Styles dated? It’s quite a long list.

Harry Styles was with Caroline Flack in 2011.

harry styles dating history

When Styles was just 17 years old, teens pining for the young man were distraught to discover he was spoken for — he was romantically linked to Caroline Flack. Flack and Styles had a significant age gap: She was in her 30s at the time and the two reportedly met while he was competing on X Factor. In her autobiography Storm in a C Cup Flack wrote: “I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines and he’d said it to friends,” as per Seventeen.

Tragically, Flack completed suicide in February of 2020 at 40 years old.

Emily Atack and Harry Styles dated in 2012.

harry styles dating history

The British actress who’s best known for her role in Inbetweeners hasn’t spoken much about her relationship with Styles but the two did date in 2012. All she said about their relationship was that it was a bit of a fling: “We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” she said in an interview with Hello!

Harry Styles and Taylor Swift were together from 2012-2013.

harry styles dating history

The mega pop-star pair didn’t date for too long but they seem to have had significant impacts on one another. The couple reportedly penned songs about the romance, Swift’s tracks “Style” and “Ready for It” are said to be about Harry, while fans swear the Dunkirk actor’s tracks “Two Ghosts” are about the Swift/Style connection.

Harry and Nicole Scherzinger dated in 2013.

harry styles dating history

People have pointed to his relationship with Nicole as being yet further evidence of Harry’s proclivity for dating women who are older than him: the two have a 16-year age difference. The Sun says the two “had a dalliance at the end of the X Factor in 2013 and met up again early last year… they hooked up over three years later when Harry had matured and was a member of the world’s biggest band.”

Harry Styles and Kendall Jenner dated from 2013-2014.

harry styles dating history

Yet another high-profile relationship, but this time, with someone who was closer to Harry’s age. Kendall is only a year older than the singer. Their commitment to one another didn’t last long (at that time), and there were plenty of reports circulating the web that they had been seen on dates with one another, according to Seventeen.

Harry was with Erin Foster in 2014.

harry styles dating history

Harry reportedly went back to dating someone older than him when he began seeing Erin Foster, the founder of Bumble, in 2014. The Daily Mail spotted the pair hanging out at a pumpkin patch in 2014 and it’s been said the two met through a mutual friend.

Harry Styles and Nadine Leopold dated in 2014-2015.

harry styles dating history

Harry was spotted going on a few froyo runs with the Austrian model, but their relationship didn’t last long — they reportedly broke up in March of 2015. The two are the same age.

Sara Sampaio and Harry dated briefly in 2015.

harry styles dating history

The Portuguese Victoria’s Secret model and Harry reportedly began seeing one another shortly after Harry and Nadine stopped dating, but just like his relationship with Nadine, he and Sara didn’t stay together for very long. She’s a little less than three years older than Harry.

Georgia Fowler and Harry were together in 2015.

harry styles dating history

The third supermodel in a row for Harry, the two were spotted together on several occasions and Georgia even shared a video online of her playing Scrabble with Styles. Georgia’s a bit more than two years older than Harry.

Harry and Kendall Jenner tried it again from 2015-2016.

harry styles dating history

The two stayed together for about a year after they reportedly hung out at a New Year’s Eve party, according to Page Six.

Harry Styles dated Tess Ward in 2017.

harry styles dating history

Harry and the popular food blogger had dated under the radar until Tess reportedly broke their relationship off and rekindled a relationship with her ex.

Camille Rowe and Harry Styles were in a relationship from 2017-2018.

harry styles dating history

The French-American model who was on the cover of Playboy in 2016 reportedly dated Harry for a full year before the two called it quits. She’s four years older than the singer.

Kiko Mizuhara and Harry dated in 2019.

harry styles dating history

Harry and Kiko were spotted at the singer’s 25th birthday party together, but there are conflicting timelines as to when they actually began dating and when they split up. Some say they were donezo in 2018, while others say 2019, which seems more likely because they were at his 25th birthday party together.

Kimberly Stewart and Harry Styles dated back in 2013.

Kimberly Stewart at the Farrah Fawcett Foundation's "Tex-Mex Fiesta" 2017 at Wallis Annenberg Center for the Performing Arts on September 9, 2017 in Los Angeles, California

Several months after splitting with Swift, Styles was reportedly dating musician Rod Stewart’s daughter Kimberly Stewart. Styles, who was 19 at the time, was first spotted with a then-33-year-old Kimberly while out to dinner with Rob and his wife Penny Lancaster. The following night, the duo were also seen at SoHo House.

“Kim and Harry looked like they were enjoying each other’s company,” a source told PEOPLE. “Age doesn’t really matter in the Stewart family.”

Felicity Skinner

Before Styles was a megastar, he met one of his first girlfriends, Felicity Skinner, through a mutual friend. The two teenagers began dating, despite living in different cities. The couple remained together for almost a year before drifting apart. Looking back on the relationship, Skinner says Styles was a great boyfriend.

“He was a really good boyfriend, very romantic and, yes, shy. He was good looking and obviously I found him very attractive. We were together for just under a year … We just clicked straight away and got on really well. He has a really cute smile. We started seeing each other when we were both about 15. He was really sweet. It was puppy love and we were definitely each other’s first loves,” Felicity shared in an interview.

Emma Ostilly

Emma Ostilly attends the 3rd annual amfAR Inspiration Gala New York at The New York Public Library - Stephen A. Schwarzman Building on June 7, 2012 in New York City

In April 2012, Styles was briefly linked to model Emma Ostilly, who was featured in One Direction’s “Gotta Be You” music video. While the group was in the middle of a world tour, Styles and Ostilly were spotted sharing a kiss following a night out in Auckland, New Zealand. The pair were reportedly seen together one other time during the trip but eventually went their separate ways.

Cara Delevingne

Image Source: Getty / David M. Benett

Styles and Cara Delevingne have been friendly for years, and while outlets like E News reported that they were dating at one point in 2013, there was never any confirmation from either party.

Kara Rose Marshall

Image Source: Getty / Karwai Tang

Styles was rumored to be dating model Kara Rose Marshall after they were seen hanging out in New York with Styles’s hairstylist back in 2013, per E News.

Paige Reifler was rumored to be in a relationship with Harry Styles in 2014.

Image Source: Getty / Gilbert Carrasquillo

In 2014, Styles was spotted in a few social media photos with model Paige Reifler before stepping out with her a couple times. However, things got messy when photos of the duo were posted by one of Styles’s friends, prompting fan outrage, per the Daily Mail. After the scandal, Reifler and Styles weren’t seen together again.

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