Pacey gets a job at a bar and meets an attractive Hispanic waitress named Karen. Although Karen has a very non-friendly boyfriend, that doesn't stop Pacey from feeling attracted to her. Dawson arrives to visit Joey, and is misled by Audrey when she decides to set her sights on him herself. Jen's compassion gets her to help Charlie and be on the college radio station.

Dawson is hit with tragedy after he heads home to Capeside to break the news to his parents that he is dropping out of USC to be with Joey, who is in shock herself after she realizes Pacey has been in Boston for weeks.

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.

Dawson is having trouble with anxiety attacks since his father's death, so he tries to escape reality on a night of debauchery with Jack and his fraternity brothers, which ends with Dawson's accusing Joey of causing his father's death.

Meanwhile, Jen seeks revenge on Charlie; Audrey's mom visits; and Pacey makes a discovery about Danny.

Jen helps Dawson go to the shrink he ran away from last week. Dawson still thinks that the whole idea of sharing his thoughts with a complete stranger is weird, but he is surprised with how much he learns from it. Back home, he has to handle the problem with his father will, which does not include Lily. Meanwhile, Joey is working on a project about old love letters written by an obscure writer, and with the help of Audrey's audition tape for ""The Real World: Ibiza"", she manages to catch something no one of the fellow students caught. Pacey confronts Karen about the risks she is taking for having an affair with Danny, and Karen is hurt when Danny's wife shows up at a dinner party and he blows her off completely.

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.

After watching scary movies, Joey, Pacey and Jack talk about their creepiest experiences and urban legends. Joey shares her story of how she was almost attacked by the librarian on Halloween and saved by the creepy man she was running from. Jack tells the story of when he was helping clean the frat house basement and found a guy strapped, who later he found out to be a ghost. Pacey reveals that he was chased by a black car while giving Karen a ride home, but there was nobody driving the car. Grams arrives and says she has the scariest story: the time when Jen got locked out of the radio booth.