Happy 28th birthday Cassie! Casandra Elizabeth Ventura, shortened as Cassie, is a Connecticut R&B singer whose first hit was “Me & U” in 2006. Starting off her industry career as a model, she appeared in Seventeen Magazine when she was only sixteen years old. At the time, she was represented by Wilhelmina Models and later on she worked with Sean ‘Diddy’ Combs on her first album.