After Dawson, Joey, Jen and Pacey individually commit various violations at school, they all get stuck together for an eight-hour Saturday of detention, along with Abby Morgan, a trouble-making imp, where tensions still run high between all of them when Dawson and Pacey turn against each other, and Joey offers a tearful, partial explanation for her personal anger towards Jen.

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.