Zimbio, in photo: Demi Moore, Emilio Estevez
3. Demi Moore was engaged to Emilio Estevez
1985 - 1987

Demi Moore and Emilio Estevez had an on-again, off-again relationship for about 2 years. They got engaged in 1985 after starring in "St. Elmo's Fire" together, a movie that helped launch both of their careers. They split in 1987 without every tying the knot.