For about two years, Jenner and Harry Styles were in an on-and-off-again relationship. The celebrity couple first fuelled dating rumours after being spotted several times together in late 2013, followed by a Mammoth ski trip over the winter holidays, per Us Weekly.
The duo kept quiet about the status of their relationship until January 2016 when they were seen holidaying on a yacht together in St. Barts. At the time, Jenner's sister Khloé Kardashian told Entertainment Tonight that she believed the two were dating, though she was unsure whether it was casual or serious.
Naturally, it was momager Kris Jenner who confirmed that her daughter had dated the former One Direction singer. While playing "Never Have My Kids Ever" on "The Ellen DeGeneres Show" in 2021, Jenner showed the "They have" card after being asked, "Never have my kids ever dated someone from a boy band." Host DeGeneres quipped back, "Well, of course, Kendall, right? And Harry?," to which Jenner smiled and responded, "Yeah."
While they're no longer together, the two are amicable. Back in 2019, Jenner and Styles played "Spill Your Guts or Fill Your Guts" on "The Late Late Show With James Corden," in which they asked each other an array of personal and funny questions.
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