Mrs. Valentine forces Joey to go on a double date with Pacey to accompany Drue and his wealthy, dim-witted, girlfriend, Anna Evans, to make sure that Drue behaves himself. Of course this isn't an easy thing to do when Joey starts to get concerned over the attention that Anna is bestowing on Pacey. Meanwhile, Dawson has his own problems when he and Gretchen go out with two of her college friends and he realizes the span in between their ages. Also, Jack finally gets some positive attention from Tobey when he asks Jack for help in teach reading to grade school kids, and Mr. Brooks becomes more weaker from his illness during the final completion on Dawson's documentary. Knowing that his days are numbered, Mr. Brooks tells Dawson to continue to follow his dream as a filmmaker and not let the love of his life (Joey) slip away, and end up like him: a bitter, misanthropic, lonely old man.

While the rest of the school goes to the snowy mountains of Vermont for a ski weekend, Dawson stays behind to help Grams keep a bedside vigil at the hospital for the near-death Mr. Brooks. But things become complicated when Dawson learns that Mr. Brooks had earlier asked him to sign a medical clause which leads him to be forced to make an impossibly hard decision to decide whether or not to cut off Brooks' life support systems. Meanwhile, the ski trip evening takes an unexpectedly romantic turn when Jen sprains her ankle, she breaks into her room's mini-bar, gets drunk and nearly sleeps with Jack. At the same time, Drue and Anna Evans sneak into the events pretending to be another couple since Drue has been banned from the ski trip and Anna does not go to school at Capeside. Also, Pacey and Joey find their own ways to keep warm on the cold night by taking their relationship to the next level.