Teenager Tom McHugh, who is quite reserved, admires his attractive neighbor Geena Matthews from afar, as she lives just across the street. However, he lacks the courage to approach her. When Tom’s parents leave town with their dog for a competition, his confident older brother, Craig McHugh, unexpectedly visits from California, bringing along a vintage 1959 Cadillac. Craig takes it upon himself to arrange a date for Tom with Geena. He lends Tom his clothes and credit card, and Tom even gets a haircut to resemble Craig. Tom also buys flowers and contacts a limousine service. Unfortunately, the limo driver gets into an accident, prompting Tom to “borrow” the classic car to impress Geena. The evening takes a dramatic turn when Tom is mistaken for Craig and discovers a body in the car’s trunk, turning what was supposed to be a dream date into a nightmare.