Joey is in her 2nd month at Worthington University where she is struggling in her beginners writing class taught by Professor David Wilder who criticizes her first essay about her and Dawson. Audrey Liddell, Joey's brash new roommate from Beverly Hills, proves to be more of an annoyance than a friend with her wild and crazy personality. Dawson, who's continuing his studies at USC with an internship in Hollywood, begins his job on a shaky start when he meets Todd Carr, an arrogant, egocentric, hack film director who gives Dawson a hard time. Meanwhile, Jen pays Pacey a visit, who's lying low as he docks his yacht in Boston Harbor after sailing away the summer. At nearby Boston Bay College, Jen and Jack are invited to their first fraternity party. They persuade Joey to come along with Audrey who seems to get along with Jen and Jack, much to Joey's surprise. Also, Jen meets Charlie, a bass player. She is rude to him, insulting him away, but deep inside feels strongly attracted to him.

Dawson goes back to Capeside to inform his parents of his decision to drop out of USC and stay in Boston. Mitch reprehends him and tells him he belongs in California, but Dawson's decision is made. Meanwhile, Jack is accepted on the Sigma Epsilon fraternity house and has doubts if he should go because they want him because he would be filling a quota of being a gay member. Joey finds Pacey working at the restaurant and goes pay him a visit on the boat where they have a nice conversation about their current lives. Pacey, bored of just peeling potatoes at the restaurant, has to put up with one waitress, named Karen Torres, and her bad mood in which he later finds out because he got the kitchen job she wanted. Also, Jen and Charlie try to go through 12 hours without sex so they can learn more about each other.

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.