After spending their first romantic night together, Dawson and Joey decide not to discuss it, because every time something happened between them they always ruined it by over discussing it. Dawson even shows Joey the set that he's working on which resembles his own house in Capeside. Meanwhile, Pacey starts on his new job as a stock broker which was set up by Audrey's father and during Pacey's first day he deals with his ambitious, but oily and pig-headed boss Rich Rinaldi. At the same time, Jack finally gets himself and Pacey the dream apartment Pacey was chasing so hard to get, with a little deviousness against Emma. During a heated argument with Grams, Jen accidentally meets a very cute guy, named C.J., a fan of Jen's defunct radio show who invites her to a counseling center that he works at. Also, Joey is hired as a waitress as the local bar, Hell's Kitchen, to get some extra cash for herself.

Joey's worst nightmare comes true when she accidentally sends a very personal e-mail she wrote for Dawson to the entire student body. The next morning, Joey's e-mail is the topic of virtually all campus discussions when Professor Hetson cruelly decides to debate it with his students just to see Joey squirm at the talk. Meanwhile, Jack makes an attempt to get to know his cultural professor, Mark Freeman, better, but he pays no attention to Jack. Pacey, while struggling to survive the first days on his new job, closes a very important deal for the firm, which his wheeling-dealing mentor Rich Rinaldi takes full credit for. Eddie, at student in Joey's reading class and whom works as the bartender at Hell's Kitchen, persuades Joey to confront any challenge that Hetson throws and not show any weakness because the stern and misogynistic Hetson thrives on it.

Dawson's former girlfriend, Natasha, (whom Dawson met and dumped during his summer in L.A.) returns as the new lead actress for the movie and now he has to deal with the consequences of dumping her over the phone. The production orders some food from Hell's Kitchen and Joey delivers it on the set, forcing her to see Dawson. Natasha gets angry and jealous when she sees Joey and has Todd fire Dawson by saying she will not work unless Dawson goes. But Natasha soon realizes Joey has hurt Dawson much more than he hurt her. When Eddie confronts Joey about her uncertainty, she decides to "follow an impulse" and kisses him. Meanwhile, Pacey ditches Audrey and goes to a strip club party with his bosses. Audrey runs into him and goes to a party with Jen and Jack, where she gets drunk and almost sleeps with a guy, if it weren't for C.J.'s stopping her. Also, Jack is disappointed when Professor Freeman tells him his wife is pregnant, and later makes a move on Jack.

Audrey gets a little too drunk before a concert with 'Hells Belles' band at Hell's Kitchen, and ends up making a scene and trashing the place. C.J., who was there on a "non-date" with Jen, tries to give her a little comfort and end up taking her back to his place. Meanwhile, Jack attends Professor Freeman's book signing and tells him the moment for Jack to make his move has passed as Freeman informs him that he has quit teaching to concentrate on his writing career. Jack then goes to invest his relationship with David, who waited all night long for Jack to show up at the bar. Joey feels bad for not being there for Audrey and has an argument with Eddie. When Eddie comes over to Joey's dorm to hand her Audrey's wallet that was forgotten at the bar, they decide drop their little game and go on a date. Also, Pacey's firm partners go down to New Orleans to celebrate a business deal, and Pacey has a big disappointment when he learns that the girl he's with is a call-girl bought by Rinaldi.

A big movie star, named Max Winter, arrives on the set to act with Natasha, and the flirting between them upsets Dawson. Pacey takes Emma to an office party where she finds out that Pacey is using her to win a contest among the office employees to see who brought the hottest date. Meanwhile, Joey has an upcoming Hetson final and Eddie offers his place for her to study. In the morning, they talk and end up having sex, which causes Joey to be late and she ends up missing the exam. Professor Hetson refuses to let Joey take a make up test and outright gives her an 'F'. Later that evening, Hetson comes to the bar and immediately starts an argument with Eddie where, in a very cruel tone, he tells Eddie how much he despises a loser like him taking up Joey's time. The hot-tempered Eddie falls right into the trap by punching Hetson in the face, and he gets instantly fired from Hell's Kitchen for it. Admired by Eddie's actions and stand against the mean Professor Heston, Joey then tries to cheer Eddie up and admire him for his noble act by taking to a local ice skating rink where they declare their love for each other.

During a typical five-day work week, Joey is incessantly trying to reach Eddie while dealing with Harley Hetson showing up at Hell's Kitchen every day after cutting school. When Harley persuades Joey to see Eddie, she is devastated after finding out that Eddie has moved out of his apartment without saying a word. But Joey manages to persuade Harley to behave like an adult, and she also finally stands up to the intimidating Professor Hetson to help him look after Harley once in a while. Meanwhile, Pacey begins skipping work by hanging out at the Boston Aquarium with Emma. But any romance between Pacey and Emma is quashed when Rich Rinaldi buries Pacey with more paperwork, making him miss his lunch date at the aquarium with Emma. Jen starts working as a peer counselor with C.J., but her personal interests get in the way of her work. Jack and David both get tested for HIV which leads to them talking about their sexual pasts. Dawson and Todd fly to Los Angeles after photography on Todd's movie, "Wicked Dead" finally wraps up. But Heather Tracy and the executive producer, Larry Newman, want Todd to re-shoot the entire ending. After Todd refuses, due to his pride and ego, he gets fired and Dawson is ordered to step in as director. Also in L.A., Audrey goes back to her roots by hanging out with her party-loving friend Jack Osbourne.

Harley tries to encourage Joey to make up with Eddie after they find him now living with his parents in nearby Worcester, and even gets him to return to her with a made-up story about Joey being pregnant. Meanwhile, Audrey returns from L.A. with a more positive attitude. After apologizing to her friends, Emma takes Audrey back in the band Hell's Belles for a big concert. But Audrey cannot stay away from liquor in which she performs drunk, and passes out on stage, and Emma fires her from the band. Meanwhile, Pacey is invited by Rinaldi to an exclusive party for the best stockbrokers and gets a promotion of handling a mysterious account led by the shady pharmaceutical entrepreneur Roger Stepavich to handle the client's major pharmaceutical company. All is well until a mysterious woman tells Pacey that all that good might have some bad, which raises suspicions on Pacey about Rinaldi's true intentions towards him.

Joey agrees to be Pacey's temporary secretary over his recent promotion. But they both have second thoughts when their mutual jealousy leads to disaster in the office over a reporter, named Sadia, the same woman whom met Pacey at the office party (in the 'All the Right Moves' episode), as well as Joey not getting along at all with the pig-headed and callous Rich Rinaldi. Meanwhile in Los Angeles, Dawson sells his idea for a coming-of-age movie, but when the studio heads Heather Tracy and Larry Newman want to change the movie into a teen sex film, Dawson must decide if he should take the lucrative deal or stick with his original concept. Also, an open-minded Grams is the intermediary that brings Jen and C.J. back together.

Joey aces Professor Hetson's final exam and ends the semester with a C+, and Joey is finally relived that her ordeal with Hetson is over. However, she decides she wants him as her advisor after she chooses English as her major. Eddie proposes they go backpacking through Europe before going their separate ways to college. Reluctant at first to jump so suddenly on such an intense trip, Joey decides to go, only to find a goodbye note from Eddie, this time for good saying that she deserves someone better than him. Elsewhere, David finally breaks up with Jack, who ponders if he was only with David to prove to himself that he could hold a steady relationship. Meanwhile, Pacey continues dating Sadia and selling stocks. But things change drastically, first when Sadia leaves him by returning to her fiancée. Then the biotech stocks that he and Dawson were investing in go bankrupt. Pacey then asks Rinaldi to borrow some money, but the cold-hearted Rinaldi refuses. Frustrated and angry, Pacey finally snaps and punches Rinaldi in the face, who instantly fires Pacey.