Harry Styles' Dating History: From Kendall Jenner to Olivia Wilde

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Everyone wants to know who Harry Styles is dating — but he's always been notoriously private regarding his love life.

Since rising to fame in One 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 late Caroline Flack. Less than a year later, his paparazzi photos with Taylor Swift went viral after the rumored couple were spotted on a date in Central Park. Styles has also been linked to several Victoria's Secret models, including Kendall Jenner and Camille Rowe.

Most recently, he dated his Don't Worry Darling costar Olivia Wilde and despite the controversy surrounding their relationship, Styles maintained his stance on keeping his romances private. I

"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 told Rolling Stone.

Now, after nearly two years together with Wilde, Styles is single again — but it sounds like fans shouldn't expect for him to make any statements about any future relationship.

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," Felicity shared in an interview.

Caroline Flack

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In 2011, Styles was linked with television personality Caroline Flack. At the time, One Direction had recently wrapped their run on The 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 autobiography Storm 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.

Flack died by suicide in 2020. Although Styles didn't speak out publicly about her death, he seemingly paid tribute to her by wearing a black ribbon to the 2020 BRIT Awards.

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 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.

Emily Atack

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The following month, rumors surfaced that Styles was seeing Inbetweeners actress Emily Atack. The pair had previously interacted on Twitter, but when dating reports made headlines, Atack said 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," Emily told Reveal magazine in 2013.

Taylor Swift

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Styles first crossed paths with Taylor Swift in March 2012, when they both attended the Nickelodeon Kids' Choice Awards. During One Direction's performance, Swift was spotted dancing in the audience.

Rumors began swirling that the couple were dating when fans noticed Styles was wearing the same paper plane necklace that Swift had worn on several occasions. Then in November, a source told PEOPLE that Styles had joined Swift while she was rehearsing for an appearance on The X Factor. Host Mario Lopez confirmed the sighting, saying that Styles had implied he was there to see Swift.

In early December, Styles and Swift were photographed together for the first time while 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.

Over the course of the month, Styles met Swift's family — and the pair even took a trip to England. The couple went on to spend the holidays together, and just before Christmas, they spent a ski vacation with pals Justin Bieber and Selena Gomez in Park City, Utah. They kicked off the new year together too, sharing a kiss after Swift's performance in Times Square. Soon after, they jetted off to the British Virgin Islands, where things took a turn in their relationship. Just days into their trip, the couple reportedly split and on January 4, Swift headed home by herself.

Following their breakup, Styles and Swift remained tight-lipped about their relationship. It wasn't until 2014 that fans got an inside look at the couple's relationship with the release of Swift's album 1989. In an interview with Rolling Stone later that year, she seemingly hinted that both "Style" and "Out of the Woods" were written about Styles. In his own Rolling Stone feature in 2017, Styles said he didn't mind if Swift wrote songs about him and opened up about the relationship for the first time. Looking back at the former couple's Central Park paparazzi photos, Styles shared that he felt like it was all a learning experience.

"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 has only had kind things to say about Swift, even stopping 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 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."

Kendall Jenner

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Styles was first linked with Kendall Jenner in 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 told Piers Morgan that he didn't know if things would turn romantic, while Jenner once again denied romance rumors at 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, they celebrated Styles' 20th birthday together.

RELATED: Harry Styles and Kendall Jenner's Relationship: A Look Back

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 joined Ellen DeGeneres on her yacht in St. Barts. While they didn't confirm their relationship at the time, Jenner's sister Khloé Kardashian offered her 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 told Entertainment Tonight. "But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

Following their vacation, the pair returned to L.A. and partied together at a friend's birthday celebration, although they attended separately. Styles and Jenner weren't spotted again until April 2016, when fans alleged they had seen the pair shopping together.

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 birthday party, but it would mark the last time they were seen together for quite a while.

In July 2018, Jenner attended Styles' concert in L.A. Then in May 2019, they bumped 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 on The Late Late Show to play a game of "Fill Your Guts or Spill Your Guts." During the segment, Jenner asked Styles which songs on his album were about her and he chose to eat cod sperm rather than admit which tracks could be about the model.

In November 2022, Jenner was spotted at another one of Styles' shows, this time joined by her sister Kylie Jenner and pal Hailey Bieber.

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 were both seen leaving The Nice Guy in L.A. Fans spotted Styles and Leopold together several times that December and in January, the musician was seen bringing balloons to Leopold's birthday celebration. They were photographed together on 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.

"Ah, don't really know anything about it. I definitely don't have a baby! The song's all about [having a baby] so I think it's highly unlikely [it's about me]," Georgia said on The Morning Show.

Tess Ward

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Following Styles' second split with Jenner, he was linked with British blogger and chef Tess Ward, whom he reportedly met through his stylist Lou Teasdale. In May 2017, the pair were spotted spending time together in London, with sources sharing that Styles and Ward had already been on "a number of dates" by then. That month, Ward put rumors into overdrive when she wore the same shirt as Styles to an event.

Their relationship didn't last long, and by June, the pair had split amid reports that Ward was back together with her ex.

Camille Rowe

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In 2017, Styles was introduced to Victoria's Secret model Camille Rowe through their mutual friend Alexa Chung. Styles initially sparked rumors that July when he was asked about Rowe during an interview with BBC1 Radio. At the time, Styles claimed not to know her while smirking at someone off-camera.

Just a few weeks later, the pair were spotted together for the first time while spending time in N.Y.C. In September, Rowe was photographed attending Styles' concert in Los Angeles and paparazzi later captured photos of the pair getting dinner together. Meanwhile, Rowe referenced having a boyfriend in 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 were photographed out to lunch and on a sushi date.

Not long after, Rowe headed to Oklahoma to begin work on a movie and Styles headed out on tour. The pair reunited in Europe, where fans noticed Rowe at numerous concerts. Styles and Rowe stuck together throughout much of the remainder of his world tour.

The duo were seen together for the final time during the last show of Styles' tour in Los Angeles that July.

Following the release of Styles' album Fine Line, fans speculated some of the songs were about their relationship. While Styles has not confirmed if anything was written about Rowe, he did include a voicemail from the model at the end of the song "Cherry." In the translation from French, Rowe can be heard saying, "Hey! Are you asleep? Oh, I'm sorry/Well, no … Nope, it's not important/Well then … We went to the beach and now we—/Perfect! Let's go!"

"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 after being 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 couple had 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 were photographed holding hands.

Following the film's wrap in February, the couple jetted to England together. They were next spotted together in July during a romantic vacation in Monte Argentario, Italy.

RELATED: Harry Styles and Olivia Wilde's Relationship Timeline

That fall, Wilde was seen showing her support for Styles at several concerts — and even donned his t-shirt during an outing in L.A. When she was asked about their romance that December, she said that she had no interest in addressing the negative attention surrounding 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 told Vogue. "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 slowly getting to know Wilde's children and 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, Styles continued to be coy about his relationship with Wilde, but shared that he fully appreciated being able to trust Wilde on the set of Don't Worry Darling, making it a "really nice experience." Despite remaining private, sources told PEOPLE that the couple were "more serious than ever" and finding ways to make it work amid their busy schedules.

getty (2) Harry Styles, Olivia Wilde

In August, Styles explained to Rolling Stone why he felt the need to be private about his relationships, sharing that he believed not talking about his personal life had only benefited him positively. Meanwhile, in another interview, Wilde said that she had no plans to talk about her relationship with 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 told Variety. "I think it's out of experience, but also just out of deep love."

The following month, the couple attended the premiere of Don't Worry Darling at the Venice Film Festival, although fans noted that the couple didn't interact much at the event. Despite rumors that they may have split, Wilde was spotted attending Styles' concert at Madison Square Garden and they were later seen sharing 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 to take a break from their relationship later 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."