A lovable loser finds his future looking up after meeting the woman of his dreams, only to find that he will have to work overtime in order to prevent true love from slipping through his fingers. Herman Spooner (Matthew Lillard) is about to turn thirty. He sells used cars for a living, and still lives at home with his parents. As much as they love him, Herman's parents have set a hard deadline for their son to strike out on his own. That line is Herman's thirtieth birthday. Even worse, Herman's boss has threatened to give him the axe should he fail to improve his numbers and move more cars. When Herman wakes up on the morning of his thirtieth birthday, he assumes that it will be one of the worst days of his life. But then he meets Rose, and all of his fears simply fade away. As the pair sets out on the perfect date, Rose drops a bombshell: she's about to leave for the Philippines. Realizing that he's got precious little time to show Rose how much he really cares, Herman casts all of his fears and doubts aside in a last ditch attempt to convince her their love was meant to be.