Toby Mastallone (Jami Gertz) wants to trade her local diner for upmarket dates in Manhattan. But what is a New Jersey schoolteacher who longs to look 'like a city girl' to do? Ever resourceful, she decides to collide her battered VW into the brand-new Mercedes that belongs to Sal (Dylan McDermott). Will her plan work? What secrets are hiding beneath Sal's slick yuppie exterior? And what will her loyal friends say?