Unusual episode about four separate plots told in chronological order rather than concurrently as in previous episodes. "About Last Night": Left behind at the ski lodge, Pacey and Joey are forced to go home by bus where they talk about their sordid night before where he is insecure about his performance and she brings up her own insecurity. "The Big Picture": In Capeside, Dawson is forced to face Mr. Brooks' death by going through his belongings with Gretchen. But soon, Dawson gets surprised to find out that he is Mr. Brooks' will and finds himself with a lot of money in his hands, and no idea of what to do with it. "Excess Baggage": As punishment for breaking into her hotel mini-bar and getting drunk during the class ski trip, Jen is forced to see a psychologist where she can discuss her "inner teen issues." But Jen finds the psychologist, Dr. Tom Frost, to know more about Jen than she does about herself. "Seems Like Old Times": Joey's path with Dawson's collide when they spend an evening catching up on the past weekend and its many happenings. Dawson thinks Joey is different in some way. Here, he asks her the big question: did she or did she not have sex with Pacey during the ski trip? Torn between hurting her best friend by being honest, or lying to him, Joey outright lies and says she didn't sleep with Pacey.

The results of the Senior Polls have ramifications for Dawson, Joey, and Pacey, as the three try to ignore the taunting of the poll master, who happens to be Drue Valentine. While Pacey and Joey try to have some time alone together at his and Gretchen's house, Dawson finds his first night alone with Gretchen more awkward than he'd expected. Gretchen becomes angry and snappish with everything after she learns that Joey lied to Dawson about having sex with Pacey. Meanwhile, Jack becomes resentful when Jen drags him along with her to follow Dr. Frost to find out more about him and they end up going to a poetry reading group to stalk him out.

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.

As Senior Ditch Day arrives, Joey is excited to find herself accompanying Jen on an excursion to New York City under the auspices of attending a college meeting. But it's not long before Joey realizes that they're there for an entirely different reason. Jen is there to meet her estranged father, Theo, where she reveals to him the roots of her self-destructive lifestyle. Meanwhile, eager to infuse their relationship with a bit of spontaneity, Gretchen and Dawson take off on their own road trip. But what starts out as unpredictable fun turns into one debacle after another when they get stuck in the middle of nowhere with a flat tire. Back in Capeside, Pacey and Drue find themselves the only seniors in school on Ditch Day. That evening, they set out for some real fun, drinking at a bar which leads to both of them getting arrested for underage drinking, leaving Pacey in serious doubt as to what his future will hold for him.