Simon Cowell's former flames

GALLERIES

Simon Cowell's former flames

Sinitta

One of Simon's best known former flames is 80s pop icon Sinitta. The duo enjoy a famously close relationship that she has described as a relationship "20-year on-off" situation. They were once engaged to be married. Their connection is professional as well as personal – Simon signed Sinitta to his record label in 1985.