6. Jaden Smith:
Kylie and Jaden Smith, the son of actors Will Smith and Jada Pinkett-Smith, allegedly dated way back in 2013. The pair got introduced to each other by Kylie's former best friend, Jordyn Woods. It's unclear exactly when they split, but they are friends, even today. They were partying together at Justin and Hailey Bieber's wedding in 2019.