Daria Morgendorffer moves from Highland, Texas(see "Beavis and Butt-head"(1993)) to a suburb called Lawndale, where she finds her sister gains instant popularity. Unaccustomed to her intelligence and sarcastic wit, Lawndale High School gives her a psychological exam where they assume she has low self-esteem, and assign her to a special class for kids with low self-esteem. There she meets student artist extrodinare Jane Lane, a girl who shares her sense of humor, her disdain for suburban banality, and her love for the tabloid TV show "Sick, Sad World." Together they ...
In appreciation for helping dimwitted cheerleader Brittany Taylor out with an art class, Daria is invited to a party held by the popular crowd in a gated community. Though uninterested and indecisive about whether or not she wants to go, she realizes that her presence there might be the perfect opportunity to humiliate Quinn, and takes Jane along with her for kicks... hopefully.
Fearing that Daria and Quinn won't be prepared for college, after meeting some clients who are preparing their three-year-old daughter for it, Helen and Jake force them into Lawndale High's college prep course, and take them on a tour of their alma mater; Middleton College. Like so many parents, they find college life has changed since they've been there, and both girls get caught up in two different activities while getting the guided tour.
Lawndale's local cybercafé has a break-in, and Mr. O'Neill thinks he can prevent future vandalism and theft by restoring it as one of the hip coffee houses of the 1960's. When Daria is forced into joining the other students into raising money for repairs, and later performing on stage with one of her essays, the kids, parents, and teachers of Lawndale have no idea what she has in store for them.
Mrs. Bennett takes her economics class on a field trip to the Mall of the Millenium. Daria and Jane want nothing to do with this trip, but have no way out of it, however all is not lost when Daria discovers Quinn and the rest of the Fashion Club skipping school there.
Desperate to avoid a meeting with a family therapist, Daria substitutes for Quinn on a babysitting gig. The family she ends up sitting for are the sickeningly-sweet Lester and Lauren Gupty, who have raised their kids Tad and Tricia into brainwashed little angels that only watch The Weather Channel on television, and avoid any sugar and junk food. It will take an artist extrordinare(yes, Jane) to rescue Daria from this nauseous night, and the Gupty kids from the sheltered lifestyle they've become so accustomed to.
When a potential new fashion club member's recent plastic surgery impresses the other members, they seek to follow in her footsteps, and pressure Quinn into doing the same, whether she needs it or not. As she tries to get Daria to help her on this quest, the doctor offers to give her some extra treatment whether she wants it or not. Will Daria enjoy watching her sister humiliate herself as she tries to get enough money to go through with the procedure? Or will she try to reason with her?
The annual teachers-verses-deejays roller hockey game is coming, and there is a good chance that the students will get to see Mr. Demartino die of an aneurysm during the game - but Daria is going to miss it because she is grounded by her parents.
Jane's brother Trent, who's also the lead singer of local grunge band Mystik Spiral is offered the chance to play in the upcoming Alternapaloosa tour. Since Daria harbor's an undeniable crush on Trent, Jane offers to pay for the gas in their van and take her for their attempted tour. The fashion club, and other Lawndale High students try to go to Alternapaloosa as well.