As the school year draws to a close, changes abound for the class of 2001. While Joey and Dawson deal with their respective break-ups, Jen makes a startling decision about her future. In his own way, Jack helps Jen to rethink it. Meanwhile, Dawson has his own decision to make with regards to Gretchen when an unusual opportunity comes their way. And when Mr. Kubelik from Worthington asks Joey to bring Pacey with her to a party for incoming freshman, which fills the pair with hope that they might be able to have a future together after all. Joey and Pacey come to terms with the end of their romance.

Dawson takes Joey up on her invitation for a weekend in Boston, but the two have reservations once there. Meanwhile, Jack is surprised when his boyfriend Tobey shows up unexpectedly forcing Jack to choose between fraternity hell week and spending time with Tobey.

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

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