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Felicity Skinner

Styles' first-ever girlfriend at age 15, Felicity, opened up about him after he got famous. "He was really sweet. He was a really good boyfriend, very romantic and, yes, shy," she said of the relationship, which lasted a little under a year.

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Caroline Flack

At the beginning of his career, Styles had a fling with the late X-Factor host, Caroline Flack. However, after One Direction's heated fans got wind of the relationship, Flack was hit with hate mail and cougar-references, stating: "None of us expected it to turn so vicious and truly nasty." The two soon became just friends.

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Lucy Horobin

Causing somewhat of a scandal, Styles was then linked to married DJ Lucy Horobin in 2011. After it was reported that the two had ended up in bed together, Twitter went into an uproar and Horobin ended up getting a divorce.

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Emma Ostilly

After pictures hit the internet of Styles kissing a mysterious blonde girl in his Range Rover, One Direction fans were once again beside themselves and the relationship fell out of the spotlight as quickly as it fell in.

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Emily Atack

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Caggie Dunlop

When Caggie was spotted with Styles in his Range Rover, relationship rumors swirled. However, whatever was going on between the two soon fizzled out, apparently due to the wrath of—you guessed it—One Direction fans.

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Cara Delevingne

After seen out and about together in 2012, rumors about something between Styles and Delevingne began. He was even seen sitting front row at her runway shows. What's better than a band boy/top model relationship? Neither ever spoke about officially being together, but Cara did once state on the subject: "I like to keep my private life private and that's all I'm going to say."

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Pixie Geldof

After the two were spotted leaving a club together in 2012, rumors of Styles and Geldof's relationship began. However, nothing was ever confirmed, and it was added to the singer's list of summer flings.

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Alexa Chung

Another rumored relationship: The paparazzi caught Styles and Chung together on Valentine's Day in 2012. Chung assured fans they were just friends, tweeting: "Sorry to all the 1D fans who followed me for Harry updates. WE ARE NOT DATING. He did make me cheese on toast though which was pretty sexy."

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Taylor Swift

One of Styles' most infamous relationships sparked when he began dating Swift in 2012. After the breakup, Taylor wrote several hits about him, including "I Knew You Were Trouble," "Out Of The Woods" and "Style," which we can only assume means things didn't end very well.

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Kimberly Stewart

Another older woman for Styles (she precedes him by 14 years), Kimberly Stewart was linked to the singer in 2013. Her father, Rod Stewart was the one to reveal the relationship, stating: "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...." he said. "Bo*****s, I've let the cat out of the bag. Harry couldn't be kinder. He is very funny guy."

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Kara Rose Marshall

When Styles was spotted around New York City in 2013 with Kara Rose Marshall, fans began to speculate if the One Directioner ditched Kimberly Stewart for the young British model. The two never confirmed their relationship, but sources claim that the two had an on again, off again relationship.

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Kendall Jenner

Styles and Jenner were first linked together in 2013—after being spotted at dinner together in Los Angeles. But Styles told Piers Morgan they weren't dating.

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Paige Reifler

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Nadine Leopold

Another day, another blonde model. The two were seen together over the course of a few months in early 2015, but there was never confirmation if they were dating or not.

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Sara Sampaio

And then there was (wait for it) another model. In June 2015, Sampaio was photographed greeting the singer outside of a New York City restaurant and then leaving his hotel the next morning.

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Georgia Fowler

Styles briefly dated Georgia Fowler around October 2015, which we know because the model shared a video of the couple playing Scrabble by a fire on Snapchat. Fans have since speculated that Style's song "Kiwi" was penned about New Zealand model.

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Kendall Jenner (Again)

Surprise! A few years after Jenner and Styles were first linked, there were rumors of a rekindled romance. In 2016, they were spotted getting cozy on a yacht, but never officially stepped out as a couple.

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Tess Ward

By 2017, the British blogger/chef and Styles were reportedly set up by the Styles's hairstylist in London. Ward sparked rumors of their relationship when she wore the singer's Gucci shirt to the Audi Polo Challenge in May. The pair parted ways in June, however, with reports that Ward was back together with her ex.

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Camille Rowe

Styles confirmed his relationship with French model Camille Rowe, which lasted from the summer of 2017 until July 2018. Not only were the two officially an item, but Styles reportedly introduced Rowe to his parents. His song "Cherry" features a voicemail that fans are convinced is Rowe at the end.

Lauren Sheffield is the Content Strategy Manager at HarpersBAZAAR.com. In addition to keeping Bazaar's Facebook and Twitter feeds updated with the latest stories, she also contributes to food, interior and travel coverage on the site. When she's not in a social media hole, you can find her in search of a new food spot, trying to perfect a cocktail recipe, or booking her next trip.  

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