Secret Love Stories of the Brat Pack: Inside the Group’s Real-Life Romances

With Brats, a new documentary about the legendary 1980s Brat Pack out on Hulu June 13, Closer revisits the group’s real-life romances.

Demi Moore and Emilio Estevez

Demi Moore was playing the troubled Jules in the 1985 hit St. Elmo’s Fire when she met Brat Packer Emilio Estevez. Fresh off her divorce from her first husband, Demi fell for the now-62-year-old and the two were in the thick of the crew’s wild partying.

Within six months they were engaged, but Demi, 61, was shocked when she discovered the Mighty Ducks star had been unfaithful. “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.,” she wrote in her 2019 memoir, Inside Out.

Worse, he’d gotten an ex-girlfriend pregnant. Devastated, Demi turned to her therapist for advice. As she recalled, the therapist was blunt.

“Ordinarily, I prefer for a patient to come to an understanding on her own,” the Striptease actress remembered being told. “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.”

The broken engagement caused enough damage for Demi, who battled addiction for years as she became one of Hollywood’s biggest stars.

“She had major trust issues after that,” an insider exclusively tells Closer. “It was a difficult time for Demi, and she did things that many considered self-destructive at the time.”

She went on to marry and divorce Bruce Willis, dad to her three kids, and Ashton Kutcher, while Emilio married and divorced Paula Abdul. Now she considers her ex a friend, says the insider. “She realizes it’s for the best they didn’t get married.”

Molly Ringwald and Anthony Michael Hall

The Queen of ’80s movies and the late director John Hughes‘ muse, Molly Ringwald “didn’t have the time of day” for Anthony Michael Hall when they costarred in 1984’s Sixteen Candles, he said, but all that changed on the Breakfast Club set the next year.

The only true high-schoolers in the cast, Molly and Anthony, both 56, spent a lot of time together. The Weird Science star’s mom — who was an extra in the movie — later recalled Molly telling her she was falling in love with Anthony.

“I said, ‘That’s so sweet — why don’t you tell him?'” she said. “The next day, they were walking around holding hands.”

Anthony called the relationship “puppy love,” but the romance was formative for Molly. “He was one of the first guys she ever dated,” an insider exclusively tells Closer. “It was hard being a teen superstar when she was very shy and introverted.”

For her, Anthony was someone who could relate to her experience. “She and Anthony found themselves in similar circumstances, having to deal with fame at such a young age,” continues the insider. “That helped them bond.”

Though their on-set romance didn’t last, the two have nothing but nice things to say about each other. “They’re still friends to this day,” says the insider. “They talk and text once in a blue moon to catch up.”

After divorcing French writer Valéry Lameignère following three years of marriage in 2022, Molly went on to wed Greek-American writer and editor Panio Gianopoulos in 2007. They have three kids.

In 2017, Anthony was sentenced to three years probation after pleading no contest to charges he assaulted a neighbor. He wed Slovak-Canadian actress Lucia Oskerova in 2020 and the pair have one son.