Trama
Still suffering from the ugly-duckling syndrome that branded his youth, Harold White (Eric Mabius) hires Annie Hayes (Brooke D’Orsay), the pretty and popular girl he knew in high school, to be his dating coach and help him shed his wallflower approach to romance. Annie even enlists her friend Kim (Kathy Najimy), a waitress at a local diner, to be Harold’s practice date. Annie draws Harold out of his shell and teaches him to win over a new love interest with the help of their shared passion for classic love songs. But when sparks unexpectedly fly between “student” and “teacher,” both Harold and Annie must learn how to make up for past mistakes if they’re going to hold onto true love.