In the peaceful coastal New England town of Capeside, Massachusetts, Dawson Leery, a 15-year-old film buff, lives a fantasy life of movies and filmmaking with his lifelong friends, tomboy Josephine "Joey" Potter and the outgoing and clownish Pacey Witter. On the day before starting the new school year as a sophomore, Dawson meets and falls for newcomer Jennifer "Jen" Lindley who arrives from New York City into the house next door to Dawson's to help her grandmother care for her invalid grandfather. Dawson's new bonding with Jen makes Joey slightly jealous which comes out during a movie outing with her, Dawson, Pacey and Jen. Meanwhile, Pacey finds himself growing in love with a new mystery woman that comes to town, Tamara Jacobs, who turns out to be the new English teacher at Capeside High School. Also, Dawson tries to get into Capeside High's film class, but is denied for being a sophomore.

It's the night of the school dance. Dawson reveals his feelings for Jen. Joey confronts Dawson's mom with what she has seen. Pacey confronts his teacher over 'that kiss'.

The class movie hits some trouble, giving Dawson an advantage. Joey falls in love with a visitor to the town. Pacey's school achievements and his relationship with Tamara intensify. Dawson brings his feelings about Jen out into the open.

Dawson turns to Jen for comfort after learning about his mom's affair with her co-anchor, Bob, as well as Joey's knowledge of it. But he regrets doing so when Jen tells him some of her own problems involving her promiscuity and the real reason her parents forced her to move to Capeside. Meanwhile, Pacey and Tamara continue to temp fate with their affair, which was compromised because Dawson accidentally videotaped it.

In honor of Friday the 13th, both the film and the date, Dawson plays practical jokes against everyone while he plans a séance for the gang to look up ghosts, until they are all spooked by reports of a serial killer heading towards Capeside. Meanwhile, Jen is asked out by a friendly jock, named Cliff, in which the date ends up at Dawson's house while Dawson, Joey, Pacey bring along a slightly-crazed young woman, named Ursula, who is running away from her psychotic boyfriend.

Professor Heston orders Joey to baby-sit for Harley to make sure she does her homework. But Joey ends up serving as relationship counselor when she finds Harley's boyfriend, Patrick, hiding in the house and he starts to drool over Joey. Meanwhile, Dawson pays a visit to his past when he's asked to speak on Mr. Gold's class at Capeside High about how it is to be working in L.A. Dawson has a student, named George, show him his movie in which he realizes that he's moved on from the teenager he once was. Pacey also returns to Capeside when his father is admitted to the hospital after suffering a heart attack where Pacey has an argument with Doug about the way Pacey's been treating the family by shutting them out, and resents the new lifestyle Pacey has.