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Carefree lady-killer Jack Jericho (Robert Downey Jr.) seduces women by the dozen. But the tables abruptly turn when he meets beautiful (and totally indifferent) museum guide Randy Jensen (Molly Ringwald), who agrees to a one-night stand and then dumps him. Stymied and completely smitten, Jack keeps pursuing Randy -- and, along the way, helps her alcoholic father erase a huge gambling debt he owes the mob.