Rockett Movado steps into the hallways of Whistling Pines, and is immediately invited by Miko Kajiyama to attend their friend Nakili Abuto's halloween party on Saturday night. Rockett, although excited, soon finds out that Ruben Rosales, who was also invited, will instead be at Max Diamond's party (which is on the same night), performing with his band Debaser. From here on out, Miko makes Rockett promise to be at Nakili's instead, even if she is invited to Max's later on. Rockett promises and leaves for her next class.
In science class, Rockett sits with Ruben, who attempts to put a (fake) frog's leg in the acid. Rockett immediately freaks out, and Dana teases her for it. Depending on the player's choice, Rockett can either let the situation drop with Dana, become ashamed about her own reaction, or retaliate; Ruben will either try to calm down the fight, if one occurs, or, stand up for Rockett. Either way, things get out of hand, and the science teacher Mr. 'Clueless' Shuliss, decides to separate them, much to Ruben and Rockett's disappointment. Depending on the player's choice (after Rockett has been moved to another group) Mavis will tell Rockett about Ruben's feelings for her, and Ruben will then find an excuse to return and try to invite Rockett to Max's party.
In the girls' bathroom, Rockett meets up with Nakili and confides in her about the party, but Dana overhears her from the stall, and comes out to confront Rockett. Rockett shares that earlier she had a nasty run-in with Dana, and would much rather stay away from her. She also mentions that she'd love to go check out DeBaser at Max's party on Saturday. The CSG girls leave, and two new girls appear, whom Rockett has never met before, up until this point. The two girls, Arianna 'Arrow' Mayfield and Viva Cortez tell Rockett that they have been hearing all about her artistic talents and would love if she'd help design some halloween costumes for them. Once again, it's up to the player to decide whether or not Rockett should respond. Whitney appears and announces that they need to go to gym soon, or they will be late.
In gym class, the students are playing soccer, and Rockett has another run-in, this time with Nicole. After this, Cleve and Mavis appear, and after talking with them a bit, Rockett is called out onto the field. Rockett can either participate or sit out on the bench (this will earn her a detention), but in any case, Max is impressed with Rockett and he invites her to his big party right on the spot. If Rockett chooses not to participate in the gym activity, she will land herself in detention, and meet up with Ruben, as well as a new character, Wolf Dubois. If she played soccer, then afterwards, in the locker room, Rockett will meet up with Jessie, and witness Sharla bullying her friend. From then on, Rockett can choose either to defend Jessie, step in as the friendly referee, or leave the situation as is. After school, Rockett must decide whether to go to Nakili's Party or Max's.
If Rockett chooses Nakili's party, she still has a way to get to Max's later on. When Rockett first arrives at Nakili's, she overhears Dana bad-mouthing her to another girl, Ginger; the player selects Rockett's next move, and whether or not she should retaliate. Nakili and Miko introduce Rockett to one of their long-time friends, Pete, who's in highschool. Whatever decision the player chooses, Rockett winds up in the bathroom, gazing into the mirror, talking with her friend Meg. Rockett wishes she would have gone to Max's instead, but Meg helps cheer her up. Jessie knocks on the door of the bathroom, and Rockett comes out to talk with her. Finally, an annoyed Miko announces that Mavis has arrived (uninvited), and won't leave until she gets to talk to Rockett. Here, the player decides if Rockett should stay at the party or leave for Max's. This is one of the final choices that decides whether or not Rockett has a good rest of the night.
Whether Rockett attended Nakili's and decided to hitch a ride with Mavis, or she just decided to come to Max's to begin with, Rockett enters the party feeling like a third wheel. Ruben, who is delighted to see her comes and talks with Rockett. Even if Rockett tries to make the most out of the night, she still decides to leave early, realizing that it's definitely not her scene, nor her crowd. Rockett journals about her party experiences and the game ends.
By accessing the Hidden Hallway, players can check out a replica of the school, view the teacher's lounge, the yearbook office, as well as the Whistling Pines' lockers and files. Inside the lockers, the player can rummage through notes, diaries, journals, and a hundred other items to find out what the students at Whistling Pines are really up to.