Brat Pack Dating History: Emilio Estevez, Rob Lowe and more

Each member of the Brat Pack has a complicated dating history – sometimes with each other.

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

“I mean, Demi and I for a while – I don’t tell stories at school – we had something for a while,” Lowe said in an episode of Kelly Ripa The “Let’s Talk Off Camera” podcast noted that the fling preceded Moore’s involvement with fellow Brat Pack members Emilio Estevez. Estevez and Moore called off their engagement in 1986.

Molly Ringwaldfor her part, date fellow Brat Pack members and The Breakfast Club costar Anthony Michael Hall.

“It’s puppy love,” Hall said Page Six in February 2020. “(Molly) didn’t have time for me when I was making it Sixteen Candles. We do it Sixteen Candles, and I annoy him! So it’s kind of funny – I was surprised when there were little things in there, but it was fun.

Keep scrolling to find out more about the Brat Pack’s love life:

Emilio Estevez

Estevez and Moore got involved in 1985 after meeting on a plane St. Elmo’s Fire. The two quickly called off their engagement the following year.

“Emilio and I had actually just sent out invitations to a party when a friend told us she’d seen him out with someone in LA,” Moore wrote in her 2019 memoir, Outsidewhy did they break up? “She denies it, of course, but I find it hard to believe her: during a two-week breakup a few months earlier, she slept with her ‘ex’ boyfriend, lied about it and then was forced to tell me. That’s when she found out she was pregnant.”

Estevez then went with an on-again-off-again partner Carey Sally, with which he shares his son Taylor and daughter Paloma, born in 1984 and 1986, respectively.

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

Anthony Michael Hall

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

“One of the funniest things that happened while making it The Breakfast Club there was Molly Ringwald cornering me in the school hallway to tell me she had a big crush on me,” Hall said Us Weekly in June 2024. “We finished dating. One could say, my character, Brian Johnson, really got the girl.

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

Nearly four years after her split from Falzone, Hall started dating Lucia Oskerova. The two got engaged in 2019 and married in 2020. They welcomed son Michael Anthony Hall II in June 2023.

related: Brat Pack Photos Through the Years: From the ’80s to Now

The Brat Pack is a moniker coined by journalist David Blum in a 1985 piece for New York Magazine – originally set to profile after Emilio Estevez. The article made waves by naming Hollywood’s young movie stars – but it took a long time to appreciate the nickname “It (…)

Rob Lowe

Followed Lowe’s brief fling with Moore after filming About Last Nighthe is linked with several high profile celebrities including Melissa Gilbert and Princess Stephanie of Monaco.

After reconnecting in the 1990s set Bad influenceLowe started dating Sheryl Berkoff. The couple married 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 said Haute Living in March 2014. “That led me to get sober, that led me to change my life – gave me everything I am now.”

Andrew McCarthy

In 1999, McCarthy married her college sweetheart Carol Schneider. They welcomed son Sam in 2002 before divorcing in 2005.

Nearly six years after the breakup, McCarthy tied the knot with Rice Doloreswith whom they share the children Willow and Rowan.

Demi Moore

For the sake of marriage 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 Matter in 1984 before becoming engaged to Estevez. Estevez and Moore ended their marriage in December 1986.

After the split from Estevez, Moore got 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 his 2019 book, OutsideMoore explained that Willis expressed insecurities about their marriage after the birth of their daughter Rumer in 1988.

“But Bruce didn’t want to be the one who left his family, who did it for his child,” she wrote. “When he went to do it Hudson Hawkthe items are in very expensive condition. I went to visit once, and, frankly, I thought they were screwed.

Moore moved with Oliver Whitcomb three years before starting a relationship with Ashton Kutcher in 2003. The two got married in 2005 before separating in November 2011.

In the memoir, Moore points out that the three men were one of the factors in why Kutcher and he called each other.

“I want to show that I can be good and fun,” he wrote, listing the type of group as a “mistake.”

After the divorce of Kutcher and Moore, they were linked Harry Morton in 2013 followed by Sean Friday in 2014 and Daniel Humm in 2022.

Judd Nelson

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

Molly Ringwald

Aside from a brief romance with Hall, Ringwald was linked to the Beastie Boys Dweezil Zappa in the ’80s before marrying VAlery Lameignere in 1999. The duo divorced in 2002. In 2007, Ringwald got married. Panio Gianopoulos and welcomed daughter Mathilda in 2003 and twins Adele and Roman in 2009.

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

“Today is the ‘holiday car’ and I have been together for 22 years,” Ringwald wrote via Instagram at the time. “Happy birthday to us! 3 kids, 3 dogs, 1 cat and lots of love. Best decision I’ve ever made. Here’s to the other 22, at least.

Ally Sheedy

In the 80s, Sheedy dated Bon Jovi guitarist Richie Sambora for a year. After a brief romance, Sheedy got married David Lansbury in 1992 and welcomed son Beckett in 1994. They split in 2008.