Dawson, Joey, Jack and Andie spend the weekend at Boston University for an advanced look at college and where Dawson has entered his Witch Island documentary in a student film festival. But he finds the reception not to his liking along with recommendations from Nikki Green, an aspiring student director of her own. Elsewhere on the campus, due to a clerical error, Joey's weekend guide is not what she expected as it turns out to be a guy, named A.J. Moller, who shares her love of the same literature. Meanwhile, Andie's pursuit for an advanced admissions interview leads her to some inspirational advice from an unlikely source: a career secretary. Also, Jack takes a risk and explores the local gay community.

Dawson experiences an identity crisis when Nikki, who happens to be Principal Green's daughter, arrives in Capeside and gives Dawson advice on his future as an aspiring young director like her. Joey experiences her own crisis when Dawson won't open up to her about the pain of his parents divorce. Meanwhile, during a weekend outdoor folk concert, Jack's first efforts to hit on another guy are rebuffed when the man, Ethan, only wants to be friends. Elsewhere in the camp, Jen realizes that she may have passed up the chance at something special with Henry. Also, Pacey and Andie uncomfortably find themselves sharing the same after school activity of planning a school play of 'Barefoot in the Park,' with Pacey in the lead role, and Andie as the assistant director.

Dawson makes the radical move of dropping out of film class to spend some time re-evaluating his teenage years against Nikki's advice. Meanwhile, Joey is torn between attending Pacey's opening night and her date with A.J., who has come to Capeside for the day. Before opening night of the school play of 'Barefoot in the Park', Andie must take over as director when the faculty director, Mr. Broderick, becomes ill and she tries to persuade Pacey to act out his feelings when he gets stage fright. Also, Jen agrees to go out on a date with Henry by taking him out to see the play. But she throws him another block by bringing Grams with her.

Joey relies on the support of Pacey and A.J. to rally the students in a major school protest against the school superintendent, Dr. Fielding, after he forces Principal Green to resign for expelling Matt Caulfield who destroyed Joey's mural after the guy's wealthy and powerful parents threaten the school board with a lawsuit. Meanwhile, Dawson and Gail both go back to their respective places in back and in front of the camera to produce a piece about the ongoing school protest which ruffles more than a few feathers of the school board hierarchy as well as Gail's old rival; a reporter named Sherry Eisle who "stole" Gail's old job back in Philadelphia and is now covering the story in her own self-serving and bias way.