Harry Styles’ Dating History: From Taylor Swift To Kendall Jenner

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Harry Styles’ love life has always been a topic of interest. Mainly because the singer-songwriter rarely opens up about his personal life.

The 26-year-old musician enjoys his privacy. But even with his down-low lifestyle, Harry has maintained a strong presence in Hollywood. If he’s not touring the world or acting with the greats, he's releasing hit songs.

It’s no surprise that Mr. Styles prefers to keep his love-life out of the media (a lot of celebrities do). But, that hasn’t stopped fans from linking him to particular women.

From Taylor Swift to Kendall Jenner, here are the ladies Harry has reportedly dated.

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Styles was in a relationship with Caroline Flack from 2011-2012. Flack, The XFactor presenter, met Harry when he was auditioning for the show.

Flack, who was 14-years his senior, received backlash for dating Styles because he was only 17-years-old at the time.

But even with the controversy surrounding their relationship, they continued dating. In fact, Caroline was Harry's first publicized romance. And even though they broke up, they ended on good terms.

Unfortunately, Caroline died on February 15, 2020, of an apparent suicide.

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Some fans think Harry and Taylor only dated to get publicity. Even if that's true, the two appeared close.

They were together between 2012-2013. And even though their romance was short-lived, they spent enough time together for Swift to write a few songs about him.

Taylor reportedly wrote “Style,” “I Knew You Were Trouble,” and “Out Of The Woods” about her relationship with Harry.

When asked by Howard Stern how he felt about being her inspiration, Harry said, “I think it's, like, flattering. "Even if the song isn't that flattering, you still spent time on it and, ultimately, using Taylor as an example, she's a great songwriter. So they're good songs."

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Rumors of a romance between Kendall and Harry started in 2013. These rumors were only fueled when Styles admitted the two “went out for dinner.”

The couple spent the end of 2013 together and by early 2014, they seemed pretty official. Especially when they were spotted skiing in Mammoth Lakes over the New Year.

The couple broke up in February of 2014 but reconciled shortly after. By December 2015, they were fully back on! BUT, broke up again in 2016.

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Besides Kendall Jenner, Harry has been linked to several models over the years, including; Cara Delevingne, Kara Rose, Sara Sampaio, Georgia Fowler, Nadine Leopold, and Camille Rowe.

Most of these relationships were short-lived, besides his romance with Camille Rowe. Rowe, a French model, dated Styles for over a year. Their relationship was apparently serious, with Camille meeting his parents.

Unfortunately, they eventually went their separate ways. And like Taylor Swift, Harry wrote a song about the relationship.

“Cherry” is reportedly about Camille. Harry even included a voicemail from the model at the end of the track.