Demi Moore and Emilio Estevez
Emilio Estevez, known for his role in iconic '80s films and as a member of the Brat Pack, had a noteworthy connection with actress Demi Moore. Their paths first crossed on the "St. Elmo's Fire" set in 1984. Estevez, brother to Charlie Sheen and son of Martin Sheen, was already a prominent figure in the entertainment industry.
The couple's relationship blossomed to the point where they got engaged. However, by 1986, they decided to call off their engagement. In the '90s, Emilio Estevez went on to marry singer and dancer Paula Abdul, while Demi Moore entered into a high-profile marriage with Bruce Willis towards the end of the '80s. Interestingly, it was revealed that Moore's therapist had warned her against marrying Estevez, adding a unique twist to their romantic history.