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Kylie Jenner and Jaden Smith (March 2013-December 2013)

Jenner reportedly started dating longtime friend and actor Smith in March 2013, with a source telling Us Weekly, "They're dating. It's new, but they've been friends forever," at the time.

Jenner, however, insisted things were friendly in interviews. In the December 2013 prom issue of Seventeen, Jenner revealed she didn't have a boyfriend, but did want the "boyfriend prom experience." She went on to describe her perfect prom date, admitting she would be glad to take a friend, and then namedropping Smith. "If I couldn't find a boyfriend, I would want to go with one of my best guy friends, like Jaden [Smith]. I know I'd have fun with him – he makes me laugh and he is a great dancer," the 16-year-old said at the time.

Little is known about the extent of Jenner and Smith's relationship, but they've seemingly remained friends throughout the years, as they're often spotted hanging out.

Image Source: Getty / Steve Granitz