The morning after, Joey and Pacey discover they've overslept and missed the bus back to Capeside. While they wait for the next one, the couple find themselves confronted with the tensions that accompany the latest development of their relationship. Meanwhile, as punishment for breaking into her hotel mini-bar during the class ski trip, Mr. Kasdan decides to send Jen to a psychologist where she can discuss her "inner teen issues."

Back in Capeside, Joey and Dawson's paths collide and they spend an evening catching up on the past weekend and its many happenings. Sensing a change in Joey's demeanor, he poses the unthinkable question, forcing Joey to consider whether honesty is the best policy. Dawson has to come to terms with Brooks' death and is surprised to discover he is in his will.

The results of the Senior Polls have ramifications for Dawson, Joey, and Pacey, as the three try to ignore the tauntings of pollmaster Drue Valentine. While Pacey and Joey try to eke out some time alone together, Dawson finds his night alone with Gretchen more awkward than he'd expected. Gretchen learns that Joey lied to Dawson about sleeping with Pacey and is angry and Joey is forcing her to lie to her boyfriend. Meanwhile, Jack's suspicious when Jen drags him on some mysterious errands, and his suspicions are confirmed when he realizes just what she's up to.

Joey receives some good college news. But while Joey glows, Dawson is forced to face a crushing rejection. Joey's elated mood, however, is tempered by a sobering realization due to the fact her sister runs a B&B she can't afford to pay the fee. ...until Dawson proposes a surprising solution, loaning her the money Mr. Brooks left for him in his will, increasing 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 to the Big Apple. A therapy session forces Jen to confront her past.

As Senior Ditch Day arrives, Joey is excited to find herself accompanying Jen on an excursion to New York 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 finally talks to her father, for the first time since she left for Capeside. Jen reveals she saw her father in bed with another woman before she left. Meanwhile, eager to infuse their relationship with a bit of spontaneity, Gretchen and Dawson take off on a road trip... But what starts out as unpredictable fun turns into one debacle after another after 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. Having had enough, they set out for some real fun, drinking at a bar in the best Drue style, leaving Pacey in serious doubt as to what his future will hold for him.