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.

Pacey hopes that an overnight camping trip by taking Dawson to their favorite childhood camping spot will help ease the pain when he prepares to tells Dawson about his romantic feelings for Joey. But their plans get interrupted when Buzz and two of his friends come along. When Dawson brings up memories about their loyal friendship, Pacey chickens out and decides not to tell Dawson. Meanwhile, Joey deals with the emotional fallout from her kiss with Pacey by spending a girls' night out with Jen and Andie. But to Jen's surprise, they stumble upon a 15th birthday party for Henry at the local roller skating rink that she was not invited to. Also, Jack clashes with his father when Ethan arrives at his house for a visit in which Ethan gets caught in the middle when Mr. McPhee bonds with him and not Jack.

Dawson, Joey and Andie prepare their own unique prom when they learn that the committee has scrutinized Jack's selected male date Ethan. Dawson, who has invited Joey to be his date, uses the special evening to try to win her back and make Pacey jealous. Andie persuades Pacey to be her escort, but her evening ends by her consoling him about his love life uncertainties. Also at the prom, Jen becomes outraged with Henry when he reveals he is leaving Capeside for the summer to attend football camp in Ohio, and Gail and Mitch celebrate their new found romance.

Pressured by two parties, Joey ultimately must choose between her love for Dawson and her new feelings for Pacey who's planning a summer getaway by sailing down the coast on his new boat, 'True Love.' Meanwhile, Grams talks about love and regret with Jen over the departed Henry, and encourages her, with Jack and Andie tagging along, for an all-night drive to Ohio so that Jen can see Henry one last time. They then take Jack to Boston to see Ethan who tells him that he has returned to his boyfriend. Mitch and Gail decide to get remarried and have the ceremony at their house with Dawson as the best man and Joey as the maid of honor. At the end, Dawson encourages Joey to make a move to follow her own path, and she runs off to join Pacey on his boat, leaving Dawson emotionally beaten and alone once again.