Biggie first saw Lil Kim during a rap battle in the streets of Brooklyn, New York, in 1993. One day, Big stopped Kim [on Fulton Street] and she spit something for him. When they first began dating, Biggie was still in a relationship with his longtime girlfriend and baby mama, Jan. Biggie eventually ended things with Jan. The relationship with Big and Kim was described by Big's friends as a simple pimp-ho dynamics. Big knew he could get away with a lot because she was looking for that strong male figure. Throughout his relationship with Kim, Big continued relationships with other women. He never hid the fact that he was with Kim. Whoever Big was involved with, he let them know, “Yes, that’s my artist, but that’s my bitch, too.”
On August 4, 1994, Biggie married singer Faith Evans. Lil Kim was not pleased, and this caused a long fued with Faith Evans, that still to this very day is not been settled.
In 1995, Big began dating rapper Charli Baltimore. Kim called Big’s house from her friend Shaka Don"s crib one day and [Philadelphia rapper] Charli [Baltimore] called back and said, “Who is this?” Kim was like, “What do you mean who is this?” Charli said Big told her that Kim was just his artist. That hurt Kim. He’s telling Kim, “I love you and I’m always going to love you.” Then he basically told her, “But I’m no good for you.” Kim would never cop to Charli’s existence. When people would ask about her and she would say, “Who?” She had some issues with her because she knew Big was crazy about Charli.
In late 1996, shortly after the birth of Biggie's son with Faith Evans was born, Kim became pregnant. Biggie convinced her to get an abortion because the timing was not right.
Biggie and Kim's relationship became volitle at times. Lil Kim said that during an argument at the studio, her and Biggie began physically fighting. She said she was knocked unconscious after biggie chocked her. Biggie died on March 9, 1997, after being shot to death.