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.

As the school year draws to a close, Joey and Dawson deal with their respective break-ups, while Jen makes a startling decision about her future when Grams announces that she is selling her house to pay for her tuition. Meanwhile, Dawson has his own decision to make with regards to Gretchen when he wants to be with her for the summer before she goes back to college. But Gretchen refuses when she sees the specter of Joey hanging over Dawson and leaves town without saying goodbye. When Mr. Kubelik from Worthington asks Joey to bring Pacey with her to a party for incoming freshman, which fills the pair with hope that they might be able to have a future together. But it's revealed that Mr. Kubelik wants Pacey to work for the summer on his boat as a deck hand.