There are two distinct narratives in the game which allow the player to play as either Brett or Becky. Both stories take place at the same locations, but under different continuities. The game is split up by different "scenes" that contain a narrative consisting of dialogue, similar to a script of an episode of a sitcom. Each scene gives the player an objective to complete. During a scene, the player will appear on the bottom screen of the Nintendo DS and the person they are talking to will appear on the top. With nearly every interaction with characters within a scene, the player is given the option from a list of responses on how to respond. Different situations will require the player to use their wit and charm, in addition to a wide variety of collectible items, to progress through the scene. There are multiple locations in the game, all of which feature their own theme music. The "mood" of the music in a scene is influenced by how characters react to choices.
Bonus scenes are unlocked through the collection of "golden lines", which are quotes that are deemed the most witty or absurd conversational options. Additional art pieces can be unlocked through the collection of various items throughout the game.