The Kardashian-Jenner family. Some love them, some hate them, and some love to hate them. Although the Kardashian and Jenner sisters are best known now for being married to Kanye West and having dalliances with famous NBA players, the sisters have a longer and more complicated dating history than most people remember. It all started when their mom, Kris Kardashian, divorce Robert Kardashian. Robert was one of OJ Simpson’s best friends and lawyers, and his children with Kris included Kim, Khloe, Kourtney, and Robert. Soon Kris married Bruce Jenner, who was then best-known as the winner of the decathlon in the 1976 Olympic Games. They would have two daughters, Kendall and Kylie.
21. Kim and TJ Jackson
Fast-forward several years: Kim was a young friend of the nefarious Paris Hilton, a hotel heiress with a reality show. While still in high school, Kim sought out opportunities to date celebrity (and celebrity-adjacent) men. Her first love was T.J. Jackson, the youngest son of Tito Jackson. This grandson of Joe Jackson and nephew of Michael was in an R&B band known as 3T. He dated Kim from 1994 to 1996. His debut album with 3T dropped right in the middle of their relationship.