As everyone gets ready for this year's senior prom which is held aboard a yacht cruising on the cape, some bad news causes Gretchen to reflect on her life, and Joey worries about Pacey's odd behavior. Meanwhile, Jen and Jack meddle in each others' lives resulting in some interesting prom dates with him being paired with Toby and she being paired with Drue. At the prom, Joey and Pacey confront once unspoken issues after a series of misfortunes incidents, in which Pacey loses his short temper and explodes at Joey saying that he will not be attending any college and resents the fact that she and everyone else is. The festivities cause conflict for Gretchen as she questions her relationship with Dawson after she tells him that she has decided to go back to college and thinks their relationship will not work out. Jen ends up getting drunk and nearly falls off the boat, but is saved by Drue who tells that despite his unwholesomeness, he does care about what happens to her, while only Jack and Tobey are the sole happy couple among their circle of friends.

After Mitch suddenly dies in a car accident, Dawson has to handle the funeral arrangements where everybody comes to give him and Gail support as Dawson tries not to breakdown upon his father's sudden death. Gail, unlike Dawson, is not holding up very well and feels sorry for six-month-old Lily, who will never know how her father was like. Everybody, including Joey, Jen, Jack, Pacey and even Grams Ryan try to comfort Dawson in their own way, and Dawson starts to blame himself for his father's death.