Dawson's therapist advises him to go to New Hampshire (where his documentary film of Arthur Brooks is being honored) and take a friend with him since he's been feeling so estranged from them. He takes Jen (who gets heartbroken after finding out that Charlie is trying to reconcile with his other girlfriend, Nora, and not her) and they pretend to be a couple, getting a very romantic honeymoon suite. Meanwhile, Jack brings Joey and Audrey to a frat party and Joey finds out they're only there for the fraternity brothers to score with them. Also, Pacey takes Karen on a non-romantic date and they accidentally sleep together, in which she reacts confused, quits her job, and hits the road.

Dawson accepts the job of directing the slightly annoying Oliver's film; Joey's night takes an unexpected turn when she finds herself kissing Professor Wilder.

Dawson begins directing Oliver's movie with Oliver playing the lead where Dawson has to deal with Audrey (who took the leading female part) as well as her complaints about Oliver's kissing skills. When Dawson discovers that Oliver has no talent in acting, he must recast the male lead role within the day and Jen comes up with the most unlikely candidate: Charlie. During the filming, Audrey has a crisis and locks herself in the bathroom because she kissed Pacey and felt like she was betraying Joey. Meanwhile, Joey feels conflicted over where to go on with her situation with Professor Wilder, but is called away from him at his out to help out with Oliver and Dawson's film to help Audrey get back on the set so they can finally finish the shooting. Also, Jack is fed up with his frat brothers after the homophobic Eric accuses Jack of making a pass at him in which Jack moves out of the frat house.

Oliver arranges a screening for their movie, which one of the guests turns out to be Amy Lloyd, movie critic for Boston Weekly, whom Oliver secretly invited for the screening and has a quarrel with Dawson. Meanwhile, Joey goes to Jen for advice on her feelings for Charlie, while Jen deals with Clifton Smalls, the new African-American boyfriend of Grams. Audrey tests Pacey's love for her by teasing him about the number of men she has had sex with. Also, Oliver decides to ask Jen out. She turns him down, but he plays her into being curious about him.

On Spring Break, the gang flies down to Florida to party at a beach house owned by Audrey's parents. Here, Audrey and Pacey go through their first relationship test when Audrey's old high school boyfriend, Chris, shows up with tickets for a concert where she is torn with the memories of the past and her present situation. Charlie unexpectedly shows up to try to spend some time with Joey, while Jen spends most of the week in bed suffering from a bad cold, and Jack spends his time getting drunk and refuses to talk about what's bothering him. Meanwhile, Dawson and Oliver are on the road driving towards New York to meet with a film agent who's interested in their movie Dawson spends the time telling Oliver his whole life story about him and Joey with hopes that there lies some reconciliation.

Charlie's band lands a deal for a tour and he asks Joey to go with him, but she doesn't want to leave college in the middle of the semester. Charlie then decides to quit the band and stay with her. But she breaks up with him so he can go with his band on tour. Meanwhile, Oliver and Dawson finally get to New York to meet with an agent. But Oliver ruins the meeting with his brazen obnoxiousness, and Dawson ends their partnership. Also, the restaurant Civilization is sold and an attractive, 30-something woman, named Alexandra 'Alex' Pearl, takes over as the new manager. She promotes Pacey as head chef, but fires Audrey and half the other employees. Pacey tries to get Audrey her job back, but all he gets is an inadvertent kiss from Alex.

With the end of the semester, Joey and Audrey pack their things and move out of their dorm room. Professor Wilder also says goodbye to Joey before he tells her that he has decided to leave Worthington to try writing novels again. In Capeside, while Audrey hangs out with Dawson, Joey decides to visit her dad in prison, only to find out he was released on parole four months ago. Meanwhile, Dawson receives a phone call from their agent saying that some big producer in Hollywood wants to make something out of their film. But Dawson doesn't know how to break the news to Oliver, whom he has barely spoken since their trip to New York. Alex is still ruling the Civilization like the devil-in-person and fires a waitress. Fed up with Alex, Pacey takes the opportunity of a meeting with investment executives to protest her employment tactics, which pushes her over the edge. Also, Jen and Jack decide to take an adventurous vacation in Costa Rica, but Grams tells Jen that her parents have invited her to spend summer at their new beach house.