The filming of Dawson's new movie brings back memories for both the filmmaker and for Joey, who grows to dislike Devon, the actress playing her, as well as Chris, who's playing Dawson. Meanwhile, Jen, now working as Dawson's producer, meets a new potential boyfriend for herself, Tyson 'Ty' Hicks, who is hired as a props man on Dawson's set, along with other Capeside High volunteers. Also, Pacey learns that Andie is bipolar after he finds antidepressants in her trash, which prompts her to believe that Pacey is more of an interference than a help in her life.

Dawson's confidence as a filmmaker is shaken when his new film class teacher, Nicole Kennedy, a Hollywood movie studio executive on sabbatical in Capeside, speaks her mind and tells him the painful truth about his new romance movie and its faults. Meanwhile, the future is unsure for Joey when she visits a Gypsy fortuneteller at the annual Capeside Fair, who advises her to be open to every new opportunity that crosses her path. Shortly after, Joey stumbles into Colin Manchester, a gorgeous photographer who brings out Joey's free-spirited side during a wild photo shoot. Also, Jen tries to persuade Grams to go out with an old flame, and Pacey becomes more uncertain about where he stands with Andie.

With Joey's father back in town after being paroled from prison, he persuades Bessie to expand the Ice House to cater weddings. Needing help, they enlist the services of the gang as staff. Andie tells Pacey that she hates weddings, but he loves them, while Joey doesn't think her ex-con father should be seen around Capside. In a comedy of errors, Jack and Dawson battle to help a scared bride, Andie and Pacey scramble to fix the wedding cake, while Mitch shows up with his new girlfriend Nicole Kennedy making Gayle sad, and Dawson angry. Also, the trouble-making Jen and Abby crash the ceremony to steal some food and liquor for another night out which eventually leads to tragedy.