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Everyone wants to know whoHarry Stylesis dating — but he’s always been notoriously private regarding his love life.
Since rising to fame inOne Direction, Styles has been in his fair share of high-profile relationships. Even early into his career, he made headlines for his romance with the lateCaroline Flack. Less than a year later, his paparazzi photos withTaylor Swiftwent viral after the rumored couple were spotted on a date in Central Park. Styles has also been linked to several Victoria’s Secret models, includingKendall JennerandCamille Rowe.
The “As It Was” singer dated hisDon’t Worry DarlingcostarOlivia Wildefor nearly two years after her very public split fromJason Sudeikis. Despite the controversy surrounding their relationship, Styles maintained his stance on keeping his romances private.
“I’ve never talked about my life away from work publicly and found that it’s benefited me positively. There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way,” Styles previously toldRolling Stone.
Roughly six months after his split from Wilde, the pop star sparked romance rumors withEmily Ratajkowskiwhen the pair werespotted kissing in Tokyo. Then, in June 2023, Styles was seen hanging out with actress Taylor Russell.
Here’s a look back at Harry Styles' dating history.
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,” Felicityshared in an interview.
Caroline Flack
Karwai Tang/WireImage
In 2011, Styles was linked with television personality Caroline Flack. At the time, One Direction had recently wrapped their run onThe X Factor,and Flack had just begun hosting a spin-off show,The Xtra Factor. The couple, who had a 14-year age gap, went on to date for several months. They split in early 2012, with Styles tweeting that it had been a “mutual decision.”
“Please know I didn’t ‘dump’ caroline. This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that,“Styles posted.
Flack looked back on the brief relationship in her 2015 autobiographyStorm in a C Cup, where she explained that things had been going well until their romance was made public. It wasn’t long before the public’s scrutiny of their age gap led to the relationship’s demise.
"We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women. It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season. After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘pervert,’ “Caroline wrote.
Emma Ostilly
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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 werespotted sharing a kissfollowing 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.
Emily Atack
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The following month, rumors surfaced that Styles was seeingInbetweenersactress Emily Atack. The pair had previouslyinteracted on Twitter, but when dating reports made headlines, Atacksaid they were just “friends.“Looking back several years later, Atack revealed that they had actually been romantic but were never serious enough to make things official.
"We were never boyfriend and girlfriend. I think that’s the first time I’ve ever admitted to what it was, because I’ve always just shrugged it off before. But I think it’s best to clear it up. So yeah, we had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions. Harry and I had a laugh. It was brief, but fun, and then we moved on,” Emilytold Reveal magazinein 2013.
Taylor Swift
David Krieger/Bauer-Griffin/GC Images
Styles first crossed paths withTaylor Swiftin March 2012, when they both attended the Nickelodeon Kids' Choice Awards. During One Direction’s performance, Swift wasspotted dancing in the audience.
Rumors began swirling that the couple were dating when fans noticed Styles was wearingthe same paper plane necklacethat Swift had worn on several occasions. Then in November, a source told PEOPLE that Styles had joined Swift while she wasrehearsing for an appearance onThe X Factor. HostMario Lopezconfirmed the sighting, saying that Styles had implied he was there to see Swift.
In early December, Styles and Swift werephotographed together for the first timewhile taking a stroll through Central Park in New York City. The following night, One Direction performed at Madison Square Garden and afterward, Swift joined Styles for an afterparty where they sang a karaoke duet of a Backstreet Boys song. Later that week, the duo was seen again while attending a party for a friend’s birthday.
“When I see photos from that day I think: Relationships are hard, at any age. And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier. I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it – I just wanted it to be a normal date,” Styles said.
Since then, Styles hasonly had kind thingsto say about Swift, evenstopping to chat with her during the 2021 Grammys.
Kimberly Stewart
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Several months after splitting with Swift, Styles was reportedly dating musician Rod Stewart’s daughterKimberly 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.”
Kendall Jenner
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Styles was first linked withKendall Jennerin November 2013, when they were seen getting dinner together in Los Angeles. At the time, sources told PEOPLE the pair were “just friends,” and Jenner tweeted that she was single. Shortly after, Styles toldPiers Morganthat he didn’t know if things would turn romantic, while Jenner once againdenied romance rumorsat the American Music Awards that month.
“We’re friends. He’s cool, yeah, he’s cool. You go out with one person, you’re automatically dating them,” Jenner shared.
Things seemed to heat up between the couple in January 2014 when they were spotted skiing and snowboarding in Mammoth, California. Sources told PEOPLE there was a lot of “flirting and smiling going on.” In February, theycelebrated Styles' 20th birthdaytogether.
Despite the connection, the duo appeared to put things on pause. Aside from a quick interaction at the 2014 British Fashion Awards, they weren’t seen together again until December 2015 while they were vacationing in Anguilla. Fans spotted them getting cozy on a yacht — and even sharing a kiss. Later in the trip, Styles and Jenner joinedEllen DeGenereson her yacht in St. Barts. While they didn’t confirm their relationship at the time, Jenner’s sisterKhloé Kardashianofferedher own insight into the relationship.
“Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend. Nowadays, I don’t know, people are weird with stuff. So I don’t know their ‘title,’ " she toldEntertainment Tonight. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”
The duo appeared to cool off once again and went their separate ways until that September, when sources said they were “trying to spend time together again.” Amid rumors that they were “rekindling their romance,” they were spotted on a dinner date at L.A. hot spot Ysabel. In November,Styles attended Jenner’s 21st birthdayparty, but it would mark the last time they were seen together for quite a while.
In July 2018,Jenner attended Styles' concertin L.A. Then in May 2019, theybumped into each other at the Met Gala, where they were photographed having a friendly conversation. Later that year, they proved they were on good terms when they both appeared onThe Late Late Showto play a game of “Fill Your Guts or Spill Your Guts.” During the segment, Jenner asked Styleswhich songs on his album were about herand he chose to eat cod sperm rather than admit which tracks could be about the model.
Nadine Leopold
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In between spending time with Jenner, Styles was briefly connected to Australian model Nadine Leopold. The pair were first spotted together in November 2014, when they wereboth seen leaving The Nice Guyin L.A. Fans spotted Styles and Leopold together several times that December and in January, the musician wasseen bringing balloonsto Leopold’s birthday celebration. They werephotographed togetheron several other occasions, including Styles' 21st birthday. The couple ultimately went their separate ways in March 2015.
Georgia Fowler
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During the fall of 2015, Styles was connected to model Georgia Fowler. The pair briefly spent time together while Styles was in New Zealand, as documented on Fowler’s Snapchat. At one point, the model shared a video playing Scrabble with the singer on her account. Although it doesn’t appear that their relationship continued after Styles headed home, some fans speculated that Styles' song “Kiwi” was about Fowler, but she says she’s not so sure.
Tess Ward
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Camille Rowe
JB Lacroix/ WireImage
In 2017, Styles was introduced to Victoria’s Secret model Camille Rowe through their mutual friendAlexa Chung. Styles initially sparked rumors that July when he was asked about Rowe during an interview withBBC1 Radio. At the time, Styles claimed not to know her while smirking at someone off-camera.
Just a few weeks later, the pair werespotted together for the first timewhile spending time in N.Y.C. In September, Rowe was photographed attending Styles' concert in Los Angeles and paparazzi later captured photos of the pairgetting dinner together. Meanwhile, Rowereferenced having a boyfriendin an interview, although she didn’t specify who it was.
Over the next few months, fans spotted Rowe at several of Styles' concerts across the US and Europe. The pair were spotted together several times in early 2018 as they werephotographed out to lunchandon a sushi date.
Not long after, Rowe headed toOklahoma to begin workon a movie and Styles headed out on tour. The pair reunited in Europe, where fansnoticed Roweat numerous concerts. Styles and Rowe stuck together throughout much of the remainder of his world tour.
The duo wereseen together for the final timeduring the last show of Styles' tour in Los Angeles that July.
“It got added in later on, and it felt so part of the song. It just felt like it needed it. We’re friends and stuff, so I asked her if it was OK. And she was OK with it,” Styles said in an interview with Apple Music’s Zane Lowe.
Olivia Wilde
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Styles met Olivia Wilde for the first time in late 2020 afterbeing cast in her film,Don’t Worry Darling. Months later, Wilde publicly announced her split from her long-time fiancé,Jason Sudeikis, although Wilde maintains that the couplehad privately gone their separate ways months prior.
In January 2021, Styles and Wilde were spotted together for the first time while attending a wedding in Montecito, California. Sources told PEOPLE the couple “were affectionate around their friends” and werephotographed holding hands.
That fall, Wilde was seen showing her support for Styles at several concerts — and evendonned his t-shirtduring an outing in L.A. When she was asked about their romance that December, she said that she had no interest inaddressing the negative attentionsurrounding their relationship.
“It’s obviously really tempting to correct a false narrative. 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,” she toldVogue. “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.”
Shortly after, a source told PEOPLE that things were serious for the couple as Styles was slowlygetting to know Wilde’s childrenand the actress had met Styles' mother.
“Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour,” the insider said. “She always seems focused on just making it all work. She is really Harry’s biggest fan.”
In April 2022, Styles released his song “As It Was,” which many fans speculated was written about his relationship with Wilde.One lyric, in particular, stood out to listeners — “I don’t wanna talk about the way that it was, leave America, two kids follow her, I don’t wanna talk about who’s doin' it first.”
In interviews, Stylescontinued to be coyabout his relationship with Wilde, but shared that he fully appreciated being able to trust Wilde on the set ofDon’t Worry Darling, making it a “really nice experience.” Despite remaining private, sources told PEOPLE that the couplewere “more serious than ever"and finding ways to make it work amid their busy schedules.
Harry Styles, Olivia Wilde.getty (2)
In August, Styles explained toRolling Stonewhy he felt the need to be private about his relationships, sharing that he believed not talking about his personal lifehad only benefited him positively. Meanwhile, in another interview, Wilde said that shehad no plans to talk about her relationshipwith Styles because she’d “never seen a relationship benefit from being dragged into the public arena.”
“We both go out of our way to protect our relationship,” she toldVariety. “I think it’s out of experience, but also just out of deep love.”
The following month, the couple attended the premiere ofDon’t Worry Darlingat theVenice Film Festival, although fans noted that the couple didn’t interact much at the event. Despite rumors that they may have split, Wilde wasspotted attending Styles' concertat Madison Square Garden and they were later seensharing a kiss in N.Y.C. Then in November, Wilde attended another one of Styles' shows in L.A.alongside her two children.
The couple ultimately decided totake a break from their relationshiplater that month. Sources told PEOPLE the decision was “amicable” as they are both busy pursuing different projects and Styles is about to head out on an international tour.
“He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A. It’s a very amicable decision. They’re still very close friends,” the source said with a friend adding, “Right now, they have different priorities that are keeping them apart.”
Emily Ratajkowski
Emily Ratajkowski.Gotham/FilmMagic
In March 2023, photos and videos captured Styles and Ratajkowskikissing in Tokyo, where the “Watermelon Sugar” singer had two back-to-back shows.
A few days after their PDA made headlines, a source told PEOPLE that Ratajkowski is “having fun” and “enjoys the attention from guys” since becoming single.
“She hooked up with Harry, but they are not in touch every day.Emily is interested in seeing him againthough,” the insider shared.
Taylor Russell
Getty
Styles and Russell were first spotted together in June 2023. A month later, the actress attended the pop star’s Vienna concert.
A month later, Styles and Russell were seenholding handswhile on a coffee run in London.
source: people.com
