Pacey is happy for his good grades, and decides to sail for celebration. Dawson, Joey and Drue are assigned for a work and Joey can't go with him. Instead, Pacey takes Jen with him. What they didn't know is that a huge storm was coming, and suddenly they have to face it. Andie is having an interview with Drue's mom for college, but her medical records get in her way. Mrs. Valentine worries about Andie's mental stability and denies her the spot. When the storm get bigger, Andie takes control of the situation and guides everybody to rescue Jen and Pacey, who admit to each other their biggest regrets in life. Jen regrets never being in love, despite her feelings for Henry, and Pacey regrets the destruction of his friendship with Dawson. Dawson and Joey go on a small boat to rescue them, and Dawson saves Pacey's life. He apologizes to Dawson for all his attitude over the past months.

Joey can't find a moment alone to study or deal with her feelings. Dawson's collaboration with Brooks begins, rejuvenating his film making spirit. Jen takes Jack to a "Gay-Straight Coalition" meeting but she seems to fit in with the crowd more than Jack does.

While the rest of the class is on the ski trip, Dawson stays behind to care for a near-death Mr. Brooks, but he's overwhelmed when he's asked to make an impossibly hard decision. Dawson is given the responsibility to decide whether to cut off Brooks' life support. Meanwhile, there's a lot more than skiing going on when the senior trip doesn't go exactly as planned. The evening takes an unexpectedly romantic turn for best friends Jack and Jen... After spraining her ankle Jen gets drunk and nearly sleeps with Jack. while Pacey and Joey find their own ways to keep warm on the cold, snowy night, taking their relationship to the next level.

The morning after, Joey and Pacey discover they've overslept and missed the bus back to Capeside. While they wait for the next one, the couple find themselves confronted with the tensions that accompany the latest development of their relationship. Meanwhile, as punishment for breaking into her hotel mini-bar during the class ski trip, Mr. Kasdan decides to send Jen to a psychologist where she can discuss her "inner teen issues."

Back in Capeside, Joey and Dawson's paths collide and they spend an evening catching up on the past weekend and its many happenings. Sensing a change in Joey's demeanor, he poses the unthinkable question, forcing Joey to consider whether honesty is the best policy. Dawson has to come to terms with Brooks' death and is surprised to discover he is in his will.

As graduation approaches, Joey has a tough time preparing her speech, and Dawson helps her find some bittersweet inspiration. Joey gets an unexpected surprise gift from her late mother. Pacey wonders if he's going to graduate at all, and he worries that his last final will be the toughest one. He walks out of it after the teacher makes a comment on him, costing him his diploma. Meanwhile, Andie McPhee returns home for the cap and gown ceremony, and is surprised to meet Jack's new boyfriend, Tobey, and a devious Drue, who has just moved to Jen's after being kicked out of his home by his mother after a fight, convinces Jen to help him pull a hilarious senior prank. Pacey tells Andie he has decided to take the job offer on a boat for the summer.