Everybody starts to think about their future, and how they are getting into college with Joey concerned about Pacey not having grades good enough to graduate and she being Number Four among the top 10 best in school. Drue makes everybody think it's Jen's birthday so he can throw a party and make the moves on her in which it's revealed that that they've known each other when he used to live back in New York. At the gathering, a worried Joey gets drunk and says some concerning things to everyone involved. Meanwhile, Andie takes over Jack's applications for college and drives him crazy with her obsession over it while he is recovering from a pulled shoulder he gets at football practice. Gretchen gets a job as the bartender at Gail's restaurant, and talks with Dawson about his life problems and hers about the real reason why she dropped out of college.

While Andie is recovering from her near-fatal drug overdose, Jack blames Jen for the incident, while Jen blames the deranged Drue for her life falling apart after he turns everyone, including Grams, against Jen by saying that she deliberately slipped Andie the ecstasy. Andie's father tells her that it would be better if she were to spend the rest of the year in Italy with her aunt, since she already has the credits required for an early graduation. Meanwhile, Joey is conflicted when she must ask Dawson to say a good word for a college acceptance form. Also, Dawson continues painting the misanthropic Mr. Brooks' house and realizes that the old man has his own personal life problems with his estranged family.

Jen reveals an important decision she's made with regards to college while Jack and Grams make a decision on their own for her. When Dawson comes up empty with answers to an important question on his college essay on registration for USC Film School, he turns to Mr. Brooks for inspiration and learns that Mr. Brooks' life in Hollywood eerily parallels Dawson's own life when Mr. Brooks left the filmmaking business after his best friend and girlfriend got together. Meanwhile, Pacey accompanies Joey to a formal party at the Yacht Club for prospective Worthington College students where the visiting dean, Walter Kubelik is impressed... with Pacey. Also, Gretchen takes over planning for Gail and Mitch's Christmas party at the restaurant where Mr. Brooks has a meeting of minds with Grams Ryan.

While Joey glows after being accepted into Worthington University, Dawson is forced to face a crushing rejection when he is denied to NYU. Joey's elated mood, however, is tempered by a sobering realization due to the fact her sister, Bessie, runs a B&B she can't afford the $15,000 tuition requirement, until Dawson proposes a surprising solution: loaning her the money Mr. Brooks left for him in his will, which increases her guilt for lying to him about sleeping with Pacey. Meanwhile, Jen and Jack have nothing but options when it comes to college. While Jack's convinced that New York is the place to go, Jen isn't so sure she's ready to return there because of unresolved issues with her parents. Jen tries asking Drue for advice on her past, but he's no help.