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Harry Styles (2013)
In late 2013, Harry Styles and Kendall Jenner sparked dating rumors after being spotted together, though they claimed to be "just friends." They vacationed together several times, including a 2016 New Year's trip to St. Barts, where they appeared close. Khloé Kardashian confirmed they were dating, even if unofficially. Though they eventually moved on, Styles and Jenner remained friendly. In 2017, Styles hinted a past relationship — widely believed to be Jenner — inspired parts of his debut album.