An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.
Still suffering from the ugly-duckling syndrome that branded his youth, Harold White (Mabius) hires Annie Hayes (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 (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.