More from EW
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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 recently turned up on Gossip Girl and Royal Pains. Later this year, he'll costar in the big-screen drama Main Street, opposite Orlando Bloom and Colin Firth.
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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, and 24. She will next be seen in Todd Haynes' HBO miniseries Mildred Pierce, starring Kate Winslet.
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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. His memoir, Stories I Only Tell My Friends, will hit stores sometime next year, and next season he will be a series regular on Parks and Recreation.
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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. His most recent film was the gritty Irish-American gangster flick The Boondock Saints II: All Saints Day.
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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. She appeared on Psych last season and can currently be seen in Todd Solondz's dysfunctional-family drama Life During Wartime.
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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). She has several films on tap, including the thriller Margin Call and the action movie Bunraku.
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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 this year's The Way, starring his father, Martin Sheen.