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.

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.

Oliver tells Dawson he's arranged a screening for their movie, which is yet to be finished. Dawson freaks out, but Joey comforts him saying the movie is brilliant. Everybody attends to the screening and solve their conflicts while waiting for it to start. Dawson meets a handful woman, and after exchanging insults she reveals herself to be Amy Lloyd, movie critic for Boston Weekly, whom Oliver secretly invited for the screening. She storms out of the theater, and it's up to Dawson to bring her back. They go out for coffee, have a heart-to-heart talk and even make out! Meanwhile, Joey is scared about her feelings towards Charlie and goes to Jen for advice. Jen says it doesn't matter if the guy is a jerk; at the end of her life there might always be a Clifton Smalls (the new African American boyfriend of Grams). Pacey asks Audrey how many men she's slept with, and she tests him by saying 27, then 57, when it was really only 5. Pacey passes the test and tells Audrey he's in love with her.

It's Spring Break and the gang goes down to Miami to party! But not everything is a reason to celebrate. Audrey and Pacey go through their first relationship test when Audrey's high school boyfriend (and her first true love) shows up with tickets for the M2M concert at an MTV event. She is torn with the memories of the past, and eventually kisses Chris, who confessed to Pacey still being in love with her. Nevertheless, Pacey stays cool about it and asks Audrey to be his official girlfriend after she confesses she loves him not Chris. Meanwhile, Dawson and Oliver hit to road to NY to meet a film agent who's interested on their movie, but never make it there. Dawson starts to tell Oliver his story with Joey and decides to surprise her in Miami, looking to reactivate their romance. But when he gets there, all he finds is a suicidal Jack (who's failing out of school and is suffering with the fact that Tobey's got a new boyfriend) and Pacey, who tells him his story with Joey is over. Charli

Charlie's band lands a deal for a tour and Charlie 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, which freaks Joey, who thinks they're jumping too many steps. She breaks up with him so he can go with his band on tour. Meanwhile, Oliver and Dawson finally get to NY to meet with an agent, but Oliver ruins the meeting. Dawson threats to end their partnership and begs for another chance. Civilization is sold and Alex Pearls takes over as the new manager. She promotes Pacey as head chef and fires Audrey. Pacey tries to get Audrey her job back, but all he gets is an inadvertent kiss from Alex.

Pacey leads a revolt against Alex at Civilization. Dawson, Joey, and Audrey return to Capeside, leaving Audrey to wonder about their pasts. Joey decides to see her father for the first time since his latest incarceration, while Dawson finally pays a visit to his father's grave. Jack and Jen wonder how they'll spend the summer.