On Dawson's advice, Joey attempts to heal the wounds of her new romance with Jack left shattered by rumor and innuendo, but when Jack confronts his innermost secrets, their lives and everyone's close to them will never be the same again. Meanwhile, for the first time in his life, Pacey stands up for what he believes in when he takes on an abusive teacher, but the consequences of his convictions are more than he could have imagined.

On the eve of Dawson's sixteenth birthday, Pacey and Andie follow her therapist's advice and throw themselves into an unabashed night of recklessness and the blues. Meanwhile, back at the Leery house, Joey is organizing a surprise party for Dawson, but the longer the guest of honor is a no show, the more she is subject to surprises of her own; Jen and Ty face up to the their potentially irreconcilable differences; and Gale and Mitch come to decisions about how to raise their son in light of their separation.

All of the gang's lives go through changes. After Andie begins seeing her dead brother Tim in the last episode, Jack and Pacey agree to call Mr. McPhee not realizing that he'll want them to be treated in Providence, not Capeside. All are stunned at the new changes and Andie and Pacey must decide if Andie's mental wellness is more important than being together. Jack also must decide whether or not to go with Andie or stay. Dawson while helping Mr. Potter extend the Ice House interviews him for a film project about his changed life, but has it changed? Jen decides to make a change so she calls her mother and inquires about returning home or visiting and is told it is inconvenient right now.

Dawson is recruited by his dad and Principal Green to produce a film for the football pep rally, but the stars of the film end up being Dawson and his lady friend Eve, not the Capeside Minutemen. Meanwhile, Pacey has enlisted Joey for assistance in bringing Andie back to Capeside, but their long-awaited reunion doesn't go exactly as Pacey had intended; and Jack comes to an unexpected understanding with his father who has returned to Capeside to be with Jack and Andie.

Pacey hopes taking Dawson to their favorite childhood camping spot will help ease the pain when he tells Dawson about his new feelings for Joey. Meanwhile, Joey deals with the emotional fallout from her kiss with Pacey by spending girls' night out with Jen and Andie, but to Jen's surprise they stumble upon a birthday party for Henry that she wasn't invited to.

After an emotional day filled with love, tears and wedding vows, Joey ultimately must choose between her love for Dawson and her new feelings for Pacey. Across town, Grams talks about love and regret with Jen, while Jack and Andie make a decision to drive all night so that Jen can see Henry one last time.

Andie gets accepted into Harvard in advance, but accomplishing what should be the biggest thing in her life doesn't exactly makes her happy. She decides to explore different paths in her life by going to a rave. In the party, Drue gives Jen drugs, and she gives it to Andie. She tries ecstasy, which has a reaction with her anti-depressives and makes a disastrous combination, which almost leads her to death. Mitch and Gail decide to keep their baby, and things get awkward during the celebration when Gretchen brings Pacey and Joey with her.

While Andie is recovering from her near-fatal drug overdose at the party, Jack blames Jen for the whole incident and is not talking to her. Jen blames the deranged Drue for her life falling apart when he turns Grams and the whole town against Jen by telling everyone that they intentionally gave Andie the drugs. After Andie comes home from the hospital, her dad tells her it would be better if she went to spend the rest of the year in Italy with her aunt, since she already has the credits required to an early graduation. Andie decides to go and plans a goodbye dinner with the whole gang. She tells them how important life is, and the valuable time they might be wasting with useless fights between natural best friends. Jack and Jen get things straight, and Andie plays a little trick to bring Dawson and Pacey together.