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Harry Styles was spotted out with Kendall Jenner for the second time this weekend, when they were photographed leaving a hotel in New York City together. How exciting! Kenry is really happening.

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Getty

Getty

Kendall is hardly Harry’s first high-profile gal pal. He was rumored to be seeing supermodel Cara Delevingne earlier this year, and of course he dated Taylor Swift for a very memorable three weeks toward the end of 2012. But the flirty One Direction dude really made headlines with his first public girlfriend, Caroline Flack.

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Caroline is a television presenter and personality in Harry’s native UK, and they started dating just as One Direction was blowing up there. The most major shocker? Caroline was 32 at the time, and Harry was… um… 17! Here’s to you, Mrs. Robinson. That’s about the age equivalent of, say, Giuliana Rancic dating Justin Bieber. Watch the video above to see how poorly Caroline was treated—on live TV!—when their relationship went public. Awk-ward.

Did you know about Harry’s relationship with Caroline? Do you think something like that would fly in the United States? Do you think Harry and Kendall are a good match? Tell us int he comments below or tweet us @OKMagazine.

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