Years Active: Aug. 2014
Probability They Were Actually Dating: 30%

Ashton Irwin wasn’t the only man linked to Kendall in the late summer of 2014. The then budding model was also linked to her first NBA player Chandler Parsons, who was 25 at the time to Kendall's 18. It was said that Kris Jenner set the two up after they were seen out at dinner. Presumably not wanting to jeopardize his $40 million dollar empire and speculated dating show, Chandler denied reports. He said that the two shared a personal trainer, and basically went out to eat with a group. Sure you did, Chandler. SURE YOU DID.