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.

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.

At her sister Bessie's persuasion, Joey goes to visit her father in prison. Dawson tags along and leading them to spend the night in a motel where he finally reveals his true romantic feelings for her, while Joey debates going to France for a semester abroad to escape from her troubled home life in Capeside. Meanwhile, Grams tries to persuade the atheist Jen to act through prayer as her comatose grandfather is admitted to the hospital. Also, the sarcastic Pacey continues quarreling with Doug over Pacey's failing grades, which all emits from Pacey's extremely low self-esteem.