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.

With Dawson and Joey back together, he decides to take her out to a romantic dinner for old time's sake. But also eating out are Mitch and Nicole. On top of that, the restaurant, not realizing that there are two Leery parties, has only has one table available, forcing all four of them to sit together which immediately lights up tension. Also at the restaurant are Jen and Gail where Dawson, Joey and Jen attempt to reunite Gail and Mitch after Nicole walks out from the constant arguing. But the ploy only works temporarily. Meanwhile, Andie begins to fall into insanity when she begins changing her hair color from blond to brown, and begins having ghostly encounters with her deceased brother, Tim, while Pacey and Jack catch on and try to confront her with her mental state.