Zack Siler is the big man on campus at his Southern Californian high school. His popular girlfriend, Taylor Vaughan, ditches him for a faded reality TV star from The Real World, Brock Hudson, whom she met on spring break in Daytona, Florida. Although bitter over the break-up, Zack consoles himself by claiming that Taylor is replaceable by any girl from the school. Zack's friend, Dean Sampson, Jr., disagrees and challenges him to a bet on whether Zack can turn any random girl into the Prom Queen within six weeks. While walking around the school, Dean picks out Laney Boggs, a "dorky", solitary, unpopular art student, as his choice for Zack.