Brat Pack Dating Histories: Emilio Estevez, Rob Lowe and More

Every member of the Brat Pack had complicated dating histories — sometimes with each other.

In October 2024, Rob Lowe shared that he and Demi Moore had a brief fling after playing love interests in the 1986 romantic comedy About Last Night.

“I mean, Demi and I briefly — I’m not telling tales out of school — we briefly had a thing,” Lowe explained on an episode of Kelly Ripa’s “Let’s Talk Off Camera” podcast, noting that the fling came before Moore’s engagement to fellow Brat Pack member Emilio Estevez. Estevez and Moore called off their engagement in 1986.

Molly Ringwald, for her part, dated fellow Brat Pack member and The Breakfast Club costar Anthony Michael Hall.

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“It was puppy love,” Hall told Page Six in February 2020. “[Molly] didn’t have the time of day for me when we made Sixteen Candles. We did Sixteen Candles, and I was annoying to her! So it was really funny — it kind of hit me by surprise when we had our little thing there, but it was fun.”

Keep scrolling to learn more about the Brat Pack’s love lives:

Emilio Estevez

Emilio Estevez.

Estevez and Moore got engaged in 1985 after meeting on the set of St. Elmo’s Fire. The twosome quickly called off their engagement the next year.

“Emilio and I 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 her 2019 memoir, Inside Out, of why they broke up. “He denied it, of course, but I was having a hard time trusting him: during a two-week breakup a few months before, he’d slept with an ‘ex’ girlfriend, lied about it and then forced to tell me the truth when he found out she was pregnant.”

Estevez then moved on with his on-again-off-again partner Carey Salley, with whom he shares son Taylor and daughter Paloma, born in 1984 and 1986, respectively.

After his split from Salley, Estevez was to married Paula Abdul from 1992 to 1994 before becoming engaged to Sonja Magdevski from 2006 to 2015.

Anthony Michael Hall

Anthony Michael Hall.

Hall had a brief fling with Ringwald after filming The Breakfast Club in 1985.

“One of the funniest things that happened during the making of The Breakfast Club was Molly Ringwald cornering me in the school hallway to tell me she had a big crush on me,” Hall told Us Weekly in June 2024. “We ended up dating. One could say, my character, Brian Johnson, actually got the girl in the end.”

Hall then moved on with Sandra Guerard from 2001 to 2006 and Diana Falzone from 2009 to 2010.

Nearly four years after his split from Falzone, Hall began dating Lucia Oskerova. The twosome got engaged in 2019 and tied the knot in 2020. They welcomed son Michael Anthony Hall II in June 2023.

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Rob Lowe

Rob Lowe.

Following Lowe’s brief fling with Moore after filming About Last Night, he was linked to several high profile celebrities including Melissa Gilbert and Princess Stephanie of Monaco.

After reconnecting on the set of 1990’s Bad Influence, Lowe began dating Sheryl Berkoff. The couple tied the knot in 1991 and welcomed son Matthew in 1993 followed by son John in 1995.

“[Our relationship] made me examine how I was living my life,” Lowe told Haute Living in March 2014. “That led me to getting sober, which led me to changing my life — giving me everything I now have.”

Andrew McCarthy

Andrew McCarthy.

In 1999, McCarthy married his college sweetheart Carol Schneider. They welcomed son Sam in 2002 before getting divorced in 2005.

Nearly six years after their split, McCarthy tied the knot with Dolores Rice, with whom he shares kids Willow and Rowan.

Demi Moore

Demi Moore.

Demi married Freddy Moore in 1980 when she was only 17. The marriage lasted until 1985. She had a brief fling with Jon Cryer while filming No Small Affair in 1984 before becoming engaged to Estevez. Estevez and Moore ended up calling off their December 1986 nuptials.

Following her split from Estevez, Moore married Bruce Willis in November 1987 and welcomed daughters Rumer, Scout and Tallulah in 1988, 1991 and 1994, respectively. They announced their separation in June 1998.

In her 2019 book, Inside Out, Moore explained that Willis expressed uncertainty about their marriage after the birth of their daughter Rumer in 1988.

“But Bruce didn’t want to be the guy who walked out on his family, who did that to his kid,” she wrote. “When he left to do Hudson Hawk, things were in a very precious state. I went over to visit once, and, frankly, I had the feeling that he had screwed around.”

Moore moved on with Oliver Whitcomb for three years before starting a relationship with Ashton Kutcher in 2003. The twosome tied the knot in 2005 before splitting in November 2011.

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In the memoir, Moore shared that threesomes were one of the factors behind why Kutcher and her called it quits.

“I wanted to show him how great and fun I could be,” she wrote, noting the group sex was a “mistake.”

After Kutcher and Moore’s divorce, she was linked to Harry Morton in 2013 followed by Sean Friday in 2014 and Daniel Humm in 2022.

Judd Nelson

Judd Nelson.

Nelson briefly dated Beverly Hills 90210 star Shannen Doherty in 1993 and moved on with Sheila Lussier from 2003 to 2005.

Molly Ringwald

Molly Ringwald.

Aside from her brief romance with Hall, Ringwald was linked to Beastie Boys musician Dweezil Zappa in the ‘80s before marrying Valery Lameignere in 1999. The duo called it quits in 2002. In 2007, Ringwald married Panio Gianopoulos and welcomed daughter Mathilda in 2003 and twins Adele and Roman in 2009.

Ringwald and Gianopoulos celebrated more than 20 years together in February 2023.

“Today the ‘getaway car’ and I are together 22 years,” Ringwald wrote via Instagram at the time. “Happy anniversary to us! 3 kids, 3 dogs, 1 cat and a lot of love. Best decision I ever made. Here’s to 22 more, at least.”

Ally Sheedy

Ally Sheedy.

In the 80s, Sheedy dated Bon Jovi’s guitarist Richie Sambora for a year. Following their brief romance, Sheedy married David Lansbury in 1992 and welcomed son Beckett in 1994. The twosome split in 2008.