Enid and Rebecca (best friends and outcasts among their class mates) graduate from high school. The class throws off their graduation hats, and Enid and Rebecca wander off in the distance and give the finger to the school they've managed to survive. After checking her diploma, Enid is angered to discover that it was awarded only conditionally and that she must attend a remedial art class that summer. Later, Enid and Rebecca attend the graduation party, where they are annoyed by various students they dont like, including Melora, an overly enthusiastic would-be actress. The next day, while in a 1950s-style diner, Enid and Rebecca decide to make a prank call to a lonely man named Seymour (Steve Buscemi) who has placed an ad in the personals section, pretending that they are the woman he is infatuated with. He shows up at the restaurant (where Enid and Becky are waiting with their friend and reluctant accomplice Josh), and Enid begins to feel sorry for him. In the next few days, Enid and Rebecca follow up on Seymour and go to look at a garage sale, where Seymour is selling vintage records from his own collection. Enid purchases one 33 1/3 RPM blues record from him. He wraps it in his own plastic bag, which delights her. Enid also begins to attend her art class, which is taught by Roberta Allsworth, an arty, self important performance artist. She dismisses Enid's talented drawings as cartoons, preferring the conceptual artwork of another student because it is "serious" and "political." Enid becomes more depressed and withdrawn. Rebecca, on the other hand, finds a job in a coffee shop and seems more and more content to lead an ordinary life. Despite her growing alienation, Enid finds some solace in her growing friendship with Seymour, becoming increasingly infatuated with him as her relationship with Rebecca fades. She learns more details about Seymour's life, including his middle management position with a fast food franchise called Cook's Chicken. Seymour informs Enid of Cook's secret racist past (it was originally called "Coon Chicken" also known as Coon Chicken Inn) after Enid discovers an old poster from Cook's depicting a grotesquely caricatured black man. Enid asks to borrow the poster and Seymour reluctantly lets her. Enid brings the poster to her art class, presenting it as a found art object. Her classmates are appalled, but Roberta is impressed with the concept behind Enid's project and later offers her a scholarship to an art college. As much as Enid grows to like Seymour, she is not entirely honest with him. First, she sets out to arrange dates for him and eventually encourages him to develop a relationship with Dana, the woman he originally became infatuated with. However, Enid becomes jealous when Dana works to end Enid's friendship with Seymour. After Seymour turns down Enid's invitation to her art class's end of term show, Enid is too upset to attend the show alone and skips it, unaware that her contribution, the racist poster, has created a scandal. The next day, Roberta tells Enid about the scandal and that she has lost the scholarship because of it. Enid goes to Seymour for solace and they have a drunken one-night stand. Seymour, whose feelings towards Dana have been fading anyway, now hopes to have a serious romantic relationship with Enid. Enid, on the other hand, flees Seymour's apartment the next morning before he awakens and refuses to take his calls. In the meantime, Enid and Rebecca get in a heated fight, and the two, who originally wanted to rent an apartment together, reconsider; Rebecca thinks she would be better off living on her own, but Enid, after discovering that she has lost the scholarship and that her father's former girlfriend is moving back, insists that she still wants to live with Becky. On the night before she is to move in with Becky she is unable to finish packing, and she does not show up at Becky's the next day. Seymour turns up though, frustrated because Enid has been ignoring his calls and he has lost his job because of the art show scandal. Becky, angered by Enid not showing up, spitefully tells him about the telephone prank she, Enid, and Josh were in on. Seymour turns up at Josh's workplace, a convenience store, to take out his anger by destroying the merchandise, but a customer intervenes and injures Seymour, putting him in the hospital. Enid visits Seymour and lets him know her true feelings for him ("You're, like, my hero!"), showing him how prominently she has featured him in her sketchbook. Enid and Rebecca also have a reconciliation of sorts, half-heartedly speaking of calling each other sometime. As time passes, Seymour has a therapy session with a bored psychiatrist to work out his issues. Enid, who is still trying to figure out what to do with her life, boards a bus once thought to be on a defunct line and the bus drives off into the distance.