Biggie Smalls, Faith Evans, and Lil' Kim
In Faith Evans' Keep the Faith: A Memoir, the R&B star claimed that while she was married to the Notorious B.I.G., she walked in on Lil' Kim in their bed, and Biggie subsequently admitted to their lengthy affair. Fortunately, the women managed to make amends. "My issues with Kim really went out the window when B.I.G. passed, to be quite honest," Evans said.
Blac Chyna, Tyga, and Rob Kardashian
The Kardashians clearly know how to keep it in the family. After Tyga got together with Kylie Jenner, Blac Chyna also pursued a Kardashian, albeit one slightly further from the limelight. Chyna was first connected to Rob in 2016 and gave birth to their daughter, Dream, later that year. They split soon afterward and are notoriously on terrible terms.