HomeCelebrityHarry Styles Dating History: Victoria's Secret Models To Musicians, Every Woman The...

    Harry Styles Dating History: Victoria’s Secret Models To Musicians, Every Woman The ‘One Direction’ Singer Has Dated

    The former One Direction member, Harry Styles, is one of the most famous pop singers of our time. Once a part of the biggest boy band in the world and now a successful solo singer, Styles has come a long way. During his musical journey of 10 years, the singer has also had a bright acting career, starring in movies like ‘Dunkirk‘ and ‘Don’t You Worry Darling’. 

    Apart from his professional life, the ‘Watermelon Sugar’ singer has also had many personal developments, of which his dating history is of a lot of interest to fans. Styles has dated actresses, singers and models. Here’s a full guide to all of his past relationships.

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    2011: Harry Styles’ First Public Relationship With Caroline Flack Was Quite Controversial

    Caroline Flack was called a pedophile for dating Harry Styles
    Caroline Flack was called a pedophile for dating Harry Styles

    Caroline and Harry started dating when he was 17 years old and she was 31 years old. They met when Caroline was a presenter at the ‘X-Factor’. She wrote in her autobiography, “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.’” They dated from 2011 to 2012.

    2012: Emma Ostilly

    Harry Styles dating history
    Harry Styles kissing Emma Ostilly

    Harry was spotted kissing the American model Emma Ostilly in New Zealand. She also appeared in One Direction’s music video ‘Gotta Be You’. Their fling was short-lived since nothing more came out of it.

    2012: Emily Atack

    All girlfriends Harry Styles has had till now
    Harry Styles and Emily Atack

    Rumours flew that Harry Styles and the British actress Emily Atack are a thing. This, however, wasn’t confirmed until 2014 when Atack confessed to Reveal Magazine, “We were never boyfriend and girlfriend…We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions.”

    2012: Caggie Dunlop

    Harry Styles and Caggie Dunlop had a brief romance
    Harry Styles and Caggie Dunlop had a brief romance

    Caggie Dunlop was in the reality show, ‘Made in Chelsea.’ Harry dated Dunlop briefly. 2012 was certainly a year of a number of flings for the singer.

    2012: Taylor Swift And Harry Styles Were A Much Talked About Couple

    Who all did Harry Styles date apart from Taylor Swift?
    Harry Styles and Taylor Swift

    It is the perfect thing to play ‘Style‘ by Taylor Swift. No wait, we could also play ‘Perfect’ by Harry Styles. We also got ‘I Knew You Were Trouble,’ by Swift, and if you needed another song, ‘Two Ghosts’ by Harry is there on the list too. The two pop singers may not have had a long-running sweet relationship but it did give their fans some really good music! It was in the December of 2012 when the two were photographed on their second date at Central Park, New York City. However, the brief romance ended just a month later when Swift broke up with him, the reason being reported that Styles “said something he shouldn’t have”.

    2013: Nicole Scherzinger

    Nicole Sherzinger and Harry Styles hooked up in 2013 when Harry was 19 and she was 35
    Harry Styles and Nicole Scherzinger

    The Sun reported in 2015 that Harry and Nicole hooked up in 2013. The two had met through ‘X-Factor’ in 2010. Nicole was a judge on it while Harry was a contestant. She was 35 while the upcoming musician was 19 when the two had their brief fling.

    2013: Kimberly Stewart

    Harry Styles dating history
    Harry Styles and Kimberly Stewart

    Kimberly and Harry never revealed their brief romance, but Kimberly’s father, singer Rod Stewart, did. Rod revealed, “His [Harry’s] car was here in the morning. Let’s put it that way. But he may just have come round to pick something up….

    2013: Kendall Jenner

    Harry Styles Dating history
    Harry Styles and Kendall Jenner

    The ‘Keeping Up With The Kardashians’ star, Kendall Jenner, and Harry Styles sparked rumors when they were spotted at a dinner in Los Angeles back in November 2013. The couple reportedly split up in February 2014.

    2014: Erin Foster

    Did Harry Styles date Erin Foster?
    Harry Styles with Erin Foster

    Harry Styles was spotted with Erin Foster, the then stepsister of Gigi and Bella Hadid. The two were seen together at a pumpkin patch in October 2014. The speculations died down as fast as they ignited since there was nothing more that came out of the relationship. Many reasoned that it might be the 12-year age gap between the two.

    2014: Nadine Leopold

    Harry Styles dated Nadine Leopold in 2014
    The singer spotted with Nadine Leopold

    Styles and Victoria’s Secret model Nadine Leopold were spotted together several times from 2014 to 2015. Their frequent dates, the first one which was snapped in November 2014, hinted things were cooking up seriously between them, but the two never spoke publicly of their relationship. They reportedly split in March 2015.

    2015: Sara Sampaio

    Harry Styles past relationships
    Harry Styles hugging Sara Sampaio

    In June 2015, the singer was spotted kissing and hugging the Portuguese model, Sara Sampaio. The next day, Sara was seen leaving Harry’s hotel in the same clothes, leading to the conclusion that the two spent the night together in an NYC hotel.

    2015: Georgia Fowler

    What all models has Harry Styles dated?
    Harry Styles and Georgia Fowler

    Seems like Harry had started a model spree because his next relationship was with the New Zealand model, Georgia Fowler. The two dated briefly back in October 2015. Fowler had even posted a video of her and Styles playing scrabble together on her Snapchat story. Many believed that Harry’s song ‘Kiwi‘ was about her.

    2015: Kendall Jenner And Harry Styles… Again!

    Kendall Jenner and Harry Styles cuddling in the yacht
    Kendall Jenner and Styles cuddling

    Kendall Jenner makes it back on the list as the two found their way to each other once again. The two were spotted celebrating New Year’s Eve on a yacht together. A week later, Kendall’s elder sister, Khloé Kardashian, confirmed the suspicions when she revealed to Entertainment Weekly, “Do I think they’re dating? Yes,” she said. “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.”

    Things seemed to have died down between the two until in April 2016 they were spotted again in LA, shopping together. However, Jenner was rumored to be dating LA Laker Jordan Clarkson. Again, in September 2016, the two were seen at dinner together. Fans suspected that they might rekindle their relationship, but that was the last they were seen together as a couple. They later reunited at the 2019 Met Gala followed by their fun game at ‘The Late Late Show With James Corden’. “Harry and Kendall are great friends and always have been,” a source told Us at the time.

    2016: Did Harry Styles Cheat On Kendall Jenner With Pandora Lennard?

    Many suspect Harry Styles cheated on Kendall Jenner with Pandora Lennard
    Harry Styles and Pandora Lennard

    During the on-and-off relationship with Kendall, Styles was seen leaving the fashion stylist, Pandora’s house after spending the night. This had happened just a few weeks after Khloé had confirmed Kendall and Harry were a thing.

    2017: Tess Ward

    Harry Styles dated Tess Ward
    Harry Styles and Tess Ward

    Us reported that Tess Ward, the London-based food blogger and Harry Styles were “casually seeing each other and [had] been on several dates”. The two met through mutual friends. Tess ended things with the singer a few weeks later and got back with her ex.

    2017: Camille Rowe And Harry Styles Dated For A Year

    Harry Styles dated Camille Rowe for a year
    Harry Styles and Camille Rowe

    The ‘Dunkirk‘ star was spotted with the French model, Camille Rowe, in July 2017 at a Fleetwood Mac concert in NYC. An eyewitness even described how the two seemed to enjoy their time together. “They looked really cozy. They seemed like they were having a good time and were enjoying each other’s company,” the source said. The two had a pretty serious relationship, as Styles had also introduced Camille to his parents. He was also spotted holding her purse, which the fans found very adorable. Unfortunately, the two called it quits after a year of dating. Styles’ collaborator, Tum Hull, told Rolling Stone in August 2019 that the breakup with Camille “had a big impact on him.”

    2021: Olivia Wilde And Harry Styles Are Going Strong

    Olivia Wilde is 'smitten' with Harry Styles
    Styles with girlfriend Olivia Wilde

    Olivia and Harry went public with their relationship at a wedding in January 2021, when they were photographed holding hands. A source told E! News, “They have gotten serious quickly and have an intense connection and bond.” The two have since then spent quality time together. They vacationed in London in April and then flew to Italy the following July. Us was informed by a source: “Olivia’s really smitten by Harry,” after the couple was spotted indulging in PDA on a yacht off the Italian coast. “He makes her really happy. It’s like he’s brought out this giddy side of her. The thing that works for them is that they don’t hide their relationship from the public. They don’t care who’s around watching them pack on the PDA,” an insider added. Currently, the two are renting a home together.

    Olivia has also directed Harry in her upcoming movie, ‘Don’t Worry Darling,’ which is set to release on September 23, 2022.

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    Aliya Khan
    Aliya Khan
    Aliya Khan is currently an undergraduate English student. Growing up, she surrounded herself with all kinds of fiction she could possible get her hands on. Indeed, she loves all things literature and music! Writing is something that came out of all the reading, and today, she is looking to pursue it professionally. Oh, and she wouldn't miss a good zombie apocalyptic series to binge watch!

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