Enid (THORA BIRCH) and her best friend Rebecca (SCARLETT JOHANSSON) are two disillusioned and sarcastic teens who've just graduated from high school and have no idea what they're going to be, or are supposed to do next. Hanging around a diner where the two observe and comment on others, the girls hope to get an apartment together, and enjoy irritating the boy of their dreams, Josh (BRAD RENFRO), where he works as a convenience store clerk.
Enid's home life doesn't provide her with much encouragement, as she and her dad (BOB BALABAN) don't really communicate that well, and she's not happy that Maxine (TERI GARR), her ex-stepmother, is back on the scene. Things get worse when she learns that she must attend summer school and take an art class taught by Roberta (ILLEANA DOUGLAS), to graduate, although the teacher does get her thinking about ways to better express herself through her artistic skills.
It's when Enid pulls a prank by answering a classified ad placed by Seymour (STEVE BUSCEMI), a lowly, middle-aged collector of 78 rpm recordings who's looking for a woman he earlier spotted, however, that the teen believes she's found a kindred spirit. Although she doesn't let on about her misleading him, Enid soon befriends Seymour and sets out to find him a woman who will love him for who and what he is.
After he eventually starts seeing Dana (STACEY TRAVIS) and Rebecca becomes fed up with the time she spends on him and not her, Enid soon realizes that the few friendships in her life are beginning to show strain. From that point on, and as she strives to remedy that, Enid continues trying to find her place in the world.