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.

After arriving in Boston to visit, Dawson sees great complications in his past relationship with Joey, who decides to drop out of Professor Wilder's writing class. But the line is incredibly long, which takes Joey all day and all the time she had to spend with Dawson, who ends up being guided around the campus by Audrey whom he confides in with his problems. Meanwhile, Jack pushes Jen into talking to Charlie, who works as the campus radio DJ, and after their first date, she ends up sleeping with him. Also, Doug pays Pacey a visit at the Boston docks and tells him about a job he can get for him at a restaurant, called Civilization, in which the chief, Danny Brecher, is a friend of Doug's. Reluctant at first, Pacey eventually gives in and gets the job after his latest girlfriend, Melanie, is forced to pay for their evening out since Pacey has no job or money.