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 and Jen realize that living together isn't as fun as they thought it would be; Jen turns her regular show at work into an advice show.

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.

Pacey's new boss, Alex, proposes more professionalism in the workplace. Audrey suspects something is going on between Pacey and Alex, leaving the future of their relationship unknown, while Pacey struggles with the growing attraction he feels for Alex. But when Alex shows up at Pacey's apartment and propositions him, Pacey learns that she is just a tease. Meanwhile, Dawson runs into Amy Lloyd, and they end up having sex at her apartment, where they talk about movies. She gives him an old Woody Allen movie and tells him that it's a gift. Dawson finds a movie she directed as a student and wants to see it, but she adamantly refuses. Also, Joey and Jack focus on studies, and while she has problems concentrating at the library, he has to catch up an entire semester and goes back to the fraternity house asking for help, but they refuse. Luckily, Eric shows up at Grams' house with the needed notes to help.

Summer is upon the gang and so they move on with their lives to follow their own plans. Joey, back at Capeside, returns to her job as a waitress at the Yacht Club; Pacey gets a new job there as a security guard and runs into Danny Brecher whom has left his wife; Dawson and Audrey are on their way to L.A.; and Jack and Jen to Costa Rica. But a few things change everybody's plans when their flights are delayed. Bessie tells Joey they got an answer from the scholarship Joey thought of applying in France (which Bessie secretly sent in without Joey's knowledge). Also Grams decides to go to Las Vegas with Clifton. Jack meets Eric at the airport, who was just coming back from his hometown where he tried coming out to his parents. Jen tells Jack to go help Eric, as she'll go help herself by going to meet her parents.