The shy teenager Tom McHugh worships his sexy neighbor Geena Matthews that lives on the other side of the street, but he does not dare to talk to her. When his parents travel with their dog for a competition and his self-confident big brother Craig McHugh unexpectedly arrives from California for a visit with a classic 1959 Cadillac, Graig decides to call Geena and schedule a date with Tom. He lends his clothes and his credit card to Tom, who cuts his hair like Craig, buy flowers while Tom calls a limousine service. However, the driver has an accident and Tom decides "to borrow" the fancy car to impress the girl. When Tom is mistakenly taken as being Craig and finds a body in the trunk, his dream-night with Geena becomes a nightmare.