Sean “Diddy” Combs & Kim Porter
Not many relationships have been more of a sad joke than this one. On and off since 1994, Kim started dating him when he was still with his ex-girlfriend and mother of his oldest biological son, Justin (Misa Hylton). Oh, Kim and Misa were friends at the time too (you already know what I’m thinking). Since then, it has been an up and down roller coaster for these two with him pushing her to the side when he’s wanted to make room for the likes of Jennifer Lopez, allegedly Cameron Diaz and of course, his other side chick Cassie. If you watch closely, Kim and Cassie even seem to split holidays to have their time with Diddy. He also has another daughter who is just a few months older than the twin girls he shares with Kim. I mean, just reading this would make me want to run for the hills from this man.