At one point in time, Emilio Estevez and Demi Moore seemed like the perfect 80s couple.
Just look at them.
While Demi has referred to her fiancé as her “first real love,” Emilio has openly
stated that he was “deeply in love”.
And although there were many beautiful moments throughout their romance, Moore eventually
had to break off her engagement with Estevez.
She was told by her therapist, “If you marry him, you’re going to ruin your life.”
Before Demi Moore and Ashton Kutcher were a thing, and before Demi Moore and Bruce Willis
were a thing, Moore was involved in another high-profile romance.
The prevailing narrative has the couple meeting on the set of the seminal Brat Pack coming-of-age
film St. Elmo’s Fire in 1984.
However, Emilio told The Washington Post that he and Demi had “known each other for a
long time,” in an interview a year later.
“I liked all my co-stars 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.
While filming the movie, Estevez and Moore realized they had a connection.
And although their characters don’t have any romantic involvement in the film, off-screen
was a whole different story.
The couple would spend practically all of their time together.
Moore has referred to Estevez as her “first love.”
She fell for his kind, generous nature and adored his family as well.
“He had a quiet confidence, which was really attractive to me,” Moore writes of Estevez.
“He seemed so grounded — and he had a great sense of humor, too.
I loved his looks: his sand-colored hair and piercing blue eyes, the lovely structure of
his face, and his chiseled features.”
Awwww was she in love or what?
In fact, things were going extremely well for the lovebirds.
He even helped the actor with her journey toward sobriety.
“Emilio and I started dating seriously after I got sober,” she writes.
“We were together for six months, and then we got engaged, and I moved in with him in
his condo in Malibu.”
Estevez was very sweet, very attentive, but according to Moore, a major factor in how
quickly they moved was that she was craving a family, and he had a close relationship
with his.
At the time of their romance and engagement, Estevez was a massive star after having starred
in the huge hit and now all-time classic, The Breakfast Club.
Moore’s star was rising after her starring turns on the daytime soap opera General Hospital
and feature films, Parasite and Blame It on Rio.
In Moore’s book, she revealed that Estevez was not her first entanglement on the St.
Elmo’s Fire set.
It turns out, she had a one-night stand with co-star Rob Lowe before meeting her future
fiancé.
According to the Orlando Sentinel, Demi said fellow Rob would later tease Estevez when
he and the Ghost star would share intimate scenes on the set of About Last Night in 1986.
“The worst part of this was that at the time I was seeing Emilio Estevez, and Rob
and Emilio were friends,” she 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.’”
Apparently, it was just a running gig, and all the parties were cordial and friendly.
And after only six months of dating, Emilio proposed to Demi.
The actor was ecstatic.
She was happy to spend the rest of her life with him and become a part of his family.
Yes, Moore wasn’t just close with Estevez, she was tight with his whole family, including
his brother and father, Charlie and Martin Sheen.
Because Demi came from an extremely chaotic household where there were no rules or structure,
she appreciated the Sheens/Estevez because they had a “no-nonsense” attitude.
In an interview with Howard Stern, she reveals that they were a blast to be around.
“The whole thing was definitely intoxicating,” Moore told 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 her book, Moore says part of the reason she fell in love with Estevez was because
of his relationship with his family.
Every weekend, to her amazement, the whole group would gather at the family home and
debate politics, led by Martin, a liberal activist.
Estevez’s family was reportedly a significant factor in Demi’s decision to accept the
actor’s proposal.
They were a “good influence” on her.
Did Moore love Estevez’s family more than she loved him?
That is the question.
With a wedding date set for December 1986, Demi and Emilio looked as if all was good
to go.
Yet slowly but surely, Estevez became less and less attentive with Moore, and she began
losing the trust she once had for her fiancé.
As it turns out, there was indeed trouble in paradise.
As time went on, The Breakfast Club actor began having affairs with other women.
“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.
According to Demi, Estevez slept with an ex-girlfriend during a two-week breakup.
He only admitted to the affair when he found out his ex was pregnant.
So needless to say, Moore had a hard time trusting him.
Understandably, she was furious and disappointed, yet she desperately wanted to make it work.
So as a result, she began seeing a therapist to help her deal with her relationship issues.
Her therapist blatantly told Moore that marrying the actor would be one huge mistake.
Demi was shocked when she was urgently advised not to go through with her wedding to Estevez.
She recalls the moment in her book, writing, “I remember the therapist saying to me after
a few sessions, “Ordinarily, I prefer for a patient to come to an understanding on her
own,” said the therapist.
“But I don’t have time to let that happen, so I just have to tell you: If you marry him
the way things are right now, you’re going to ruin your life.”
After the session, her therapist wanted to meet Estevez, so they could all talk it out.
She wanted to meet him, so he could “communicate his priorities directly, in person.”
The actor had no desire to do so, but hesitantly tagged along to her therapy session.
Sadly, that’s when Moore discovered how low she was on the list of her fiancé’s
priorities.
“You’ll be shocked to hear — I was pretty low on the list,” Moore wrote.
“I postponed the wedding indefinitely.”
Despite Estevez’s desperate attempts to win her back, the two had a civil split.
They remained friends and continued to attend events as each other’s dates.
And their 1987 outing to the premiere of Estevez’s film, Stakeout, actually served as Moore’s
introduction to her future husband, Bruce Willis.
In her book, she recalled Estevez telling her of Willis, “He’s all over you, like
a cheap suit in the rain.”
Two decades later, Moore went on to star in Estevez’s film Bobby, portraying an alcoholic
singer whose career was failing.
“I think he really has an ability to create,” Moore said of her ex.
Several years after splitting from Moore, Estevez was briefly married to Paula Abdul.
And he also shares two adult children with model Carey Salley.
Moore went on to marry and divorce Bruce Willis, with whom she shares three daughters: Rumer
, Scout and Tallulah.
And, of course, who doesn’t remember her tumultuous marriage to Ashton Kutcher.
Excluding Kutcher, Moore has a habit of staying close friends with her exes.
She is notably great friends with Willis.
Demi even quarantined with him, their daughters and his current wife in April 2020.
The 58-year-old opened up about the experience during her appearance on Naomi Campbell's
YouTube series No Filter with Naomi, sharing that their time together was one of the "blessings"
to have come from global crisis.
"It's everything that's come forward has allowed us to reevaluate what's important and what
needs attention that has been overlooked and neglected.
It was amazing," the mother of three continued.
Moore and Willis were self-isolated with their daughters at the Idaho home where they had
raised their children before their divorce.
Willis' wife Emma and their two daughters — Evelyn Penn and Mabel Ray — were able
to join the group a bit later when the kids were finished with school.
"It's important for the little ones to feel comfortable with me, and to know me, so they
also know their sisters better," Moore said.
"It was really sweet, and we did have some silly times, for sure."
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