The main character, Roger, is a parking enforcement officer who feels stuck in his dead-end job and in his love life. He has been pining over his neighbor, Amanda, for years but has never had the confidence to ask her out.
Desperate for a change, Roger enrolls in a class called "Building Confidence and Self-Esteem" taught by the suave and charismatic Dr. P. Although the class initially seems helpful, Roger soon realizes that Dr. P's teachings are more focused on manipulating others and gaining power than genuine confidence building.
As the class progresses, Dr. P takes a particular interest in Roger's love life and encourages him to pursue Amanda. However, things become complicated when it is revealed that Dr. P is also interested in Amanda and is using Roger to gain her affections.
The competition between Roger and Dr. P heats up, with both of them resorting to some underhanded tactics to win over Amanda. Eventually, Roger realizes that he doesn't want to win over Amanda through manipulations and decides to be honest with her about his feelings.
In the end, Roger and Amanda end up together, while Dr. P's true agenda is exposed and he is left alone. The movie ultimately shows that true confidence and self-esteem come from being genuine and honest, rather than being manipulative or deceitful.