Years Active: Winter 2014 and Spring 2016
Probability They Were Actually Dating: 35%

Sadly, Kendall has been rumored to have dated Chris Brown twice, which is two times too many. For reasons that my poor brain can’t comprehend, Chris Brown has been a Kardashian/Jenner family friend who has gotten too close to the youngest set of Jenners during their most formative years. In 2014, rumors included details that Kendall was interested in Chris for his looks and the probable exposure she’d get from dating him. In 2016, the details include sheer lunacy and lack of guidance. It's also worth notiong that Chris is one of Tyga’s near and dear friends, which may add to the validity of these reports.