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ANDREW MCCARTHY AS KEVIN
Then: His character was all about his desires: the secret (Ally Sheedy's Leslie) and not-so secret (to write something other than obits) ones.
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Now: The Pretty in Pink and Weekend at Bernie's star has turned up on the small screen with roles in Gossip Girl and Royal Pains. He costarred in the 2010 big-screen drama Main Street, opposite Orlando Bloom and Colin Firth, and was recently in ABC's now-canceled drama The Family.
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MARE WINNINGHAM AS WENDY
Then: Winnigham's virgin Wendy yearned to break free of her parents and run straight into the arms of Billy (Rob Lowe).
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Now: Returning to her small-screen roots, Winningham has guest-starred on Grey's Anatomy, Boston Legal, 24, and Todd Haynes' HBO miniseries Mildred Pierce. Most recently, she has had recurring roles on Showtime's The Affair and FX's American Horror Story.
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ROB LOWE AS BILLY
Then: He was the restless sax player who was buckling under the weight of a grown-up life.
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Now: After appearing in more than two dozen movies, the actor found his biggest success on TV with The West Wing and Brothers & Sisters. After a six-season run on Parks and Recreation, Lowe nabbed a Golden Globe nomination for his role in the well-regarded, yet now-canceled Fox series The Grinder.
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JUDD NELSON AS ALEC
Then: His smarmy, intense Capitol Hill overachiever just couldn't close the deal with Leslie.
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Now: Nelson was a regular on the series Suddenly Susan and has since popped up in a slew of TV shows and movies. He appeared in the 2009 gritty Irish-American gangster flick The Boondock Saints II: All Saints Day, and was a recurring character during the first season of Empire.
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ALLY SHEEDY AS LESLIE
Then: Leslie was a woman with a plan for the future — even if she couldn't decide if that future included marriage to Judd Nelson's Alec.
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Now: With the 1998 art-house hit High Art, Sheedy became a darling of the indie-festival circuit. Following big screen roles in Life During Wartime and Welcome to the Rileys, Sheedy had a recurring role on USA's Psych and made a cameo appearance in 2016's X-Men: Apocalypse.
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DEMI MOORE AS JULES
Then: Her sexy, little-girl-lost Jules had bad taste in men and a sweet tooth for the wild life.
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Now: Moore went on to become one of the biggest female box office stars of the '90s (Ghost, Indecent Proposal, Disclosure). However her most recent big screen work (Flawless, The Joneses, Margin Call) have not garnered nearly as much success. Moore is set for her first-ever recurring TV role for season 4 of Fox's hit series Empire.
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EMILIO ESTEVEZ AS KIRBY
Then: Kirby was a waiter/wannabe lawyer intent on impressing the girl of his dreams (Andie MacDowell).
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Now: Estevez has continued to work steadily, not only in front of the camera but also behind it as the screenwriter and director of 2006's Bobby and 2010's The Way, starring his father, Martin Sheen. He wrote the screenplay for the upcoming film The Public, in which he also stars, directs, and produces.