Cassie and Diddy first met in 2009, when she was 19 years old and he was 37 years old. He signed the Connecticut native to his Bad Boy Records label, which produced her debut and only studio album ...

Cassie met Combs in 2005, when she was 19 and just at the start of a career as a singer, model and actor. She had a hit song, “Me & U,” in 2006 off an album released by Combs' Bad Boy Records.