Being touted as "your chance to re-live your high school days," Brooktown High places the gamer in the shoes of either a male or female high school student. This character is customizable, to some extent - you can change your hair style and color, eye color, height and weight. You will also be asked several personal questions at the beginning of the game to categorize you into one of the social cliques.

The player then gets to interact with the 20 other students at Brooktown, who have their own social circles and distinct personalities, in order to become part of the different cliques. There are four different cliques: Nerds, Jocks, Preps, and Rebels.

The main goal is to find a boyfriend or girlfriend, whom you can then take on dates to various locations such the movies, the beach, and the mall. Sometimes you will also be asked a favor, and if you agree to do this, the student whom you helped might give you someone's phone number.

Various mini-games will be used to reach the goals mentioned above. Each game boosts some percentage of your clique points (for example, smarts points to get into the nerds clique and athletic points to get into the jocks clique).