Dawson takes Jen on a road trip to a small film festival in New Hampshire where his documentary is being honored. The spotlight is intoxicating for both of them as they share one of the single most momentous events in a boy's life.

Meanwhile, Jack brings Joey and Audrey to a frat party under false pretenses; and Pacey takes Karen on a non-romantic date.

Dawson and Jen realize that living together is not as much fun as they hoped to be. Between ruined toothbrushes and bathroom overcrowding, they're getting on each other's nerves. Jen faces a new challenge at work after she turns her regular show into an advice show. She mainly gives advice to other girls with problems, and makes statements on men that hurt Dawson's feelings. She comes home expecting a fight, but Dawson surprises her saying he won't fight or lie or cheat on her. Meanwhile, Melanie (Pacey's summer flame) shows up offering Pacey a job working with her uncle's new boat around the Greek Islands. After a lot of thinking, Pacey decides not to go, since he has developed a successful life in Boston working at the Civilization. Jack moves into the fraternity house and gets his own room, but has some problems staying there after he discovers he was supposed to be rooming with another guy who felt uncomfortable living with a gay guy. And Joey decides to give Elliott Sawyer another

It's Dawson's first day in his new film school. Oliver (the somewhat obnoxious filmmaker Dawson met on the film festival) starts showing him around and wastes no time in asking Dawson to direct a movie he wrote. Reluctant to direct someone else's work, Dawson starts giving notes to Oliver on the script, and ends up accepting the job, thanks to Jen's incentive. Jen, on the other hand, is having some problems of her own. Her current state of happiness from the wonderful relationship with Dawson is reflecting on her on-air performance. Now she has to go back to the sharp-tongued, edgy advices she used to give instead of the romantic, love-themed ones. Meanwhile, Elliot finally has the courage to ask Joey out, but Joey makes second plans for a gathering with professor Wilder. She makes a fake excuse not to go out with Elliot, and her evening takes an unexpected turn when she and professor Wilder kiss. Elsewhere, Jack is reprehended by his brothers for being on academic probation. Irritated

Directing Oliver's movie is not an easy task. First, Dawson has to deal with Audrey's (who took the leading part) complaints about Oliver's kissing skills. Then he has to recast the other lead role after watching the footage and discovering that Oliver stinks as an actor. Now they have to find someone who can act, is hot, charismatic in less then 6 hours. They can't think of anyone but Charlie, who fits the profile like a glove (for Jen's desperation). During the shooting Audrey has a crisis and locks herself in the bathroom because she kissed Pacey and felt like she was betraying her best. They have to call Joey (who was over at Professor Wilder's house to solve their issue) for help, and after her blessing Audrey is back on the set so they can finally finish the shooting. Meanwhile, Jack is fed up with his brothers and decides to move out of the fraternity house after he and Eric have a moment and later Eric accuses him of trying to kiss him to the other guys.

Pacey's new boss proposes more professionalism in the workplace and promises to leave behind her attraction towards him, even offering Audrey her job back. Audrey suspects something is going on between them and refuses to return to Civilization. Later, Alex drops by at Pacey's and Audrey walks on them talking about their kiss. She storms out in anger, leaving the future of their relationship unknown while Pacey struggles with the growing attraction he feels for Alex. Meanwhile, Dawson runs into Amy Lloyd, the movie critic, and they end up in bed together. After sex, they talk about movies and she lends him her movie. Joey and Jack focus on studies, and while she has problems concentrating, he has to catch up an entire semester and even goes back to the fraternity house asking for help. Luckily, Eric (the same guy that caused Jack his expulsion) shows up at Grams with the needed notes.

As summer approaches, everyone gets ready for various travels. Dawson prepares to head out for LA with Audrey, while Jack and Jen get ready for their Costa Rica vacation. Left behind in Capeside for the summer, Joey and Pacey lament their fates - until they make a crucial last-minute decision that changes everything.