1Felicity Skinner
CourtesyStyles' 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.
2Caroline Flack
At the beginning of his career, Styles had a fling with 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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3Lucy 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.
4Emma 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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6Caggie Dunlop
When Caggie was spotted with Harry 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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7Cara Delevingne
After seen out and about together in 2012, rumors about something between Harry and Cara 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."
8Pixie Geldof
After the two were spotted leaving a club together in 2012, rumors of Harry and Pixie's relationship began. However, nothing was ever confirmed, and it was added to Harry's list of summer flings.
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9Alexa Chung
Another rumored relationship: The paparazzi caught Harry and Alexa together on Valentine's Day in 2012. Alexa assured they were just friends, tweeting: "I AM NOT DATING @Harry_Styles! Ps Sorry @Harry_Styles, fancy a date?"
10Taylor 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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11Kimberly Stewart
Another older woman for Harry (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 a very funny guy."
12Daisy Lowe
Styles and Lowe were rumored to be dating after they were spotted out together numerous times, but neither ever commented on the relationship. While they do have mutual acquaintances and really could just be friends, it's safe to say that the singer has a penchant for models.
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13Erin Foster
Though the paparazzi never caught PDA pics of the two, they were spotted spending time together on multiple occasions in 2014.
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15Nadine 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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