Everything in earnest, young Gilly Noble's (Chris Klein) life is finally going right. He's got a job he enjoys, he's marrying Jo (Heather Graham), the girl of his dreams, and he's just a step away from finding his birth parents. But all that comes to a crashing halt and a year later, after losing his job and his girl, Gil sets out to get back Jo and make his life right again. The problem is, Jo has gotten engaged in their time apart, and her wealthy husband-to-be and social climbing mother (Sally Field) are not about to let Gilly take her back without a fight. Chaos ensues as our hero finds himself in one comical predicament after another, all this to win back his true love.