The LIFE Picture Collection via Getty Images Emilio Estevez, Demi Moore
Who: SAG Award-nominated actor, writer, and director Emilio Estevez, 58, and Golden Globe-nominated actress Demi Moore, 58.
How They Met: Though the prevailing narrative has the Brat Packers meeting on the set of St. Elmo's Fire in 1984, Estevez told The Washington Post that he and Moore had "known each other for a long time," in a 1985 interview.
"I liked all my costars and remained close to some of them today, but the person who stands out from this period is, of course, Emilio," Moore wrote of filming St. Elmo's Fire in her 2019 memoir, Inside Out.
Within six months of dating, the couple was engaged.
Why We Loved Them: Moore wasn't just close with Estevez, she was tight with his whole family, which included his brother and father, Charlie and Martin Sheen.
"The whole thing was definitely intoxicating," Moore told Howard Stern of her introduction to Estevez's clan. "Because it was seeing something that was very clearly different than what I had. And seeing how they were these formidable parental figures, and that they had influence and guidance, and I just really appreciated how they were."
In fact, Estevez's family was reportedly a major factor in Moore's decision to accept the actor's proposal. They were a "good influence" on her.
When They Peaked: According to the Orlando Sentinel, Moore said fellow Brat Pack member Rob Lowe would tease Estevez when he and the Ghost star would share intimate scenes on the set of About Last Night ...
"The worst part of this was that at the time I was seeing Emilio Estevez, and Rob and Emilio were friends," Moore said. "So, at the end of every day of shooting love scenes, Rob would call up Emilio and say, 'Hey, guess what I did all day? I spent the entire day in bed with Demi. Ha-ha.'"
The Breakup: The engagement was short-lived.
"Emilio and I had in fact just mailed out the invitations for our wedding when a friend told me she had seen him out with someone else in L.A.," Moore wrote in Inside Out.
Oh, and it gets worse.
RELATED: TBT: Paula Abdul and Emilio Estevez's Romance Began Over the Phone
"He denied it, of course, but I was having a hard time trusting him," she continued, "during a two-week breakup a few months before, he'd slept with an 'ex' girlfriend, lied about it, and then been forced to tell me the truth when he found out she was pregnant."
When the two met with Moore's therapist, Estevez shared his priorities. "You'll be shocked to hear — I was pretty low on the list," Moore wrote. "I postponed the wedding indefinitely."
Estevez and Moore remained friends and their 1987 outing to the premiere of Estevez's film, Stakeout, actually served as Moore's introduction to her future husband, Bruce Willis.
Two decades later, Estevez directed Moore (and her third husband, Ashton Kutcher) in Bobby.
"I think he really has an ability to create," Moore said of her ex.
Where They Are Now: Several years after splitting from Moore, Estevez was briefly married to Paula Abdul. He shares two adult children (Taylor, 36, and Paloma, 35) with model Carey Salley.
Estevez currently stars in Disney+ series The Mighty Ducks: Game Changers.
RELATED: TBT: Bruce Willis Really Went Off on Monogamy When He Was Married to Demi Moore
Moore went on to marry and divorce both Willis (with whom she shares three daughters: Rumer, 32, Scout, 29, and Tallulah, 27) and Kutcher.
Next up for the actress is drama Please Baby Please, alongside Mary Lynn Rajskub and Andrea Riseborough.
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Demi Moore Postponed Her Wedding to Emilio Estevez Because She Was “Very Low” on His Priority List - Yahoo Lifestyle
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