Kendall Jenner
From the famous and influential Kardashian-Jenner clan, Kendall Jenner went from being a reality show star to becoming a supermodel. Due to her prominence and status, her past relationships were closely monitored and heavily scrutinized by the media. From her short-lived romance with former One Direction member Harry Styles until the very recent dating rumors with the rapper ASAP Rocky, her dating life was documented just as much as her family life. She stars in one of the longest-running and most successful reality shows ever Keeping Up With The Kardashians together with her parents; Caitlyn Jenner with Kris Jenner, along with her equally famous sisters Kim, Khloe, Kourtney as well as Kylie and brother Rob. Right now, she is very much single.