Who is Kendall Jenner really dating? Kendall Jenner's love life is hard to follow. Weeks ago, the 20-year-old Keeping Up With the Kardashians star and model was rumored to be dating Jordan Clarkson, whom she'd been linked to since March, but since then, she has been linked to rapper A$AP Rocky, and in an odd turn of events, she was spotted out with Tyler the Creator days ago.