Young Dan Newman, a certified 'nice guy', is sick and tired of always finishing last. He is frustrated by watching all of the good' girls he likes date 'bad boys'. Dan's nice ways also have a detrimental effect on his career. At the office and among his co-workers, he gets no respect. Dan decides to enter into therapy with the controversial Dr. Leroy Brown - a psychologist with rather unorthodox but popular therapeutic practices. With Dr. Brown's assistance, Dan meets and dates Sharon B. Good, a 'good girl' who likes 'bad boys'. Dan falls for Sharon and in his hilarious attempt to win her over he transforms into a 'bad boy', setting the stage for both of them to learn important lessons.
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