Emilio Estevez and Demi Moore
Emilio Estevez and Demi Moore met while filming St. Elmo’s Fire and just six months after they started dating, they became engaged. Moore got very close with his family during this time as well. While mailing out wedding invitations, Moore was told by a friend that she had seen Emilio out with someone else, leading them to break up.
Emilio Estevez and Demi Moore (Terry McGinnis/WireImage)
Tyra Banks and Seal
Although Seal was most notably linked with fellow Victoria’s Secret model Heidi Klum, in 1996, he actually dated Tyra Banks as well. Following the end of her relationship with John Singleton, she and Seal attended the Essence Awards together.
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Tyra Banks And Seal (Alamy)
