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.

Joey decides to help throw a surprise birthday party for Pacey with his mother, not knowing about Pacey's 'birthday curse'. The party goes haywire as Pacey's family makes everyone feel uncomfortable, and Pacey a loser.

Dawson becomes upset when he feels that Gretchen doesn't want anyone to know about their relationship and postpones their first real date to go to the party.

The senior trip is coming up and Joey needs to get the time off from work -not an easy task seeing that Drue's mom is her boss. However, she decides to give her a few days off.... if she agrees to go on a double date with Pacey to accompany Drue and a wealthy girl named Anna Evans and make sure that Drue behaves himself. Of course this isn't an easy thing to do, and during their night out, Joey starts to get concerned over all the attention that Anna is bestowing on Pacey.

Dawson has his own problems when he and Gretchen go out with her friends and he realizes the span in between their ages. Jack also (finally) gets some positive attention from Tobey.

As Gale's delivery date approaches, the girls throw a baby shower for her...but it's an experience that throws Joey for a loop when she realizes it's possible that she could be pregnant, and Pacey is nowhere to be found. After many false alarms, Gail throws a baby name shower to try and think for a name for the baby, and the baby is born. While Dawson awaits the arrival of his new sibling, Dawson and Gretchen wonder what their future holds when Gretchen considers an out-of-town job... Meanwhile, Jack faces an unexpected situation when he learns that Tobey falls victim to a vicious crime.

As everyone gets ready for this year's senior prom, some bad news causes Gretchen to reflect on her life, and Joey worries about Pacey's odd behavior. Meanwhile, Jen and Jack meddle in each others' lives... resulting in some interesting prom dates. At the prom Joey and Pacey confront once unspoken issues, and the festivities cause conflict for Gretchen, as she questions her relationship with Dawson, while an unhappy Jen is rescued by an unlikely individual after she and Jack arrange dates for each other. Jen decides to drown her sorrows.

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.

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.