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When he has trouble getting a date, Silverman (Biggs) is set up by his lifelong best friends (Zahn, Black) with the girl of his dreams, Judith (Peet). However, they soon discover that Judith is a control freak who hates their guts, and wants to marry Silverman.

Now to get him back, his friends must take desperate measures to separate the two and have him fall for one of his past girlfriends, Sandy (Detmer). Unfortunately Silverman still thinks he's in love with Judith.