On their first day at Lawndale High, Daria and Quinn have to take a mandatory psychological exam, where perky, popular Quinn passes with flying colors, while sarcastic loner Daria is forced to enroll in a self-esteem course, where she meets the equally sarcastic Jane. Meanwhile, Quinn goes to great lengths to prevent people from knowing she's related to Daria, since she thinks that it will ruin her popularity.

After Daria helps dimwitted cheerleader Brittany in art class, Brittany invites her to her party. Daria doesn't want to go at first, but then decides to after seeing it as a good chance to embarrass Quinn, who is also attending.

Daria and Quinn get enrolled in a college-prep course, where they are given the assignment of visiting the college of their choice. Their parents decide to take them to their alma mater, Middleton College. Things start to go wrong after Daria goes into business writing term papers for cash, and Quinn gets elected 'keg queen' at a frat party.

The school starts a fundraiser to build a student coffeehouse, and after Daria and Jane fail at selling candy bars, Daria is asked to perform on stage opening night to earn the extra credit points. She ends up reciting an anti-communist story she wrote that starts a riot and has the place closed down.

Daria's class takes a field trip to the enormous Mall of the Millennium, much to Daria and Jane's dismay. Meanwhile, Quinn and her friends, the Fashion Club, ditch school to go to the same mall, but get in trouble when they run into Daria there.

Talent scouts from the Amazon Modeling Agency come to Lawndale High to teach a class on modeling, promising a modeling scholarship to one lucky student. Many of the girls in school are more than eager to get that scholarship. Daria is not one of those girls.

Mrs. Barch, a science teacher who despises men thanks to her bitter divorce, has her class pair up to do a rat-in-a-maze project. Daria is paired with dimwitted jock Kevin, whom she distracts with the Pigskin Channel while she does all the work herself. Kevin's girlfriend Brittany, meanwhile, is paired with the sleazy Upchuck, who makes Brittany his slave by blackmailing her with a picture he took of her and some guy in the backseat of a car. At Daria's house, Quinn hits on Kevin nonstop, and jealous Brittany becomes convinced that both Morgendorffers are trying to steal him from her.

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.

Brooke, a Fashion Club hopeful, gets a nose job, and Quinn is deemed shallow for saying the new nose is merely 'cute'. The other Fashion Club members subsequently also get nose jobs, and so Quinn goes to get one too, but the doctor plays on Quinn's insecurities and talks her into getting about 00 worth of surgery. Quinn doesn't have that kind of money, and becomes more determined to get it after Brooke has further surgery done and looks gorgeous. It's up to Daria to convince her she's perfect and doesn't need to change a thing.

After Daria and Quinn both come home past curfew, Helen and Jake begin Family Court, a mock trial that ends with the 2 girls being sentenced to a month's grounding. The parents later regret their decision after Daria uses this as an opportunity to drive them insane.

Daria and Jane head off to Alternapalooza with Jane's brother Trent and his friend Jesse. Daria finds this to be an awkward experience due to her strong attraction to Trent. The Fashion Club, meanwhile, dress 'alternative' and head off to the festival, but on the way, they decide to go outlet shopping instead. Back home, Helen and Jake use their kids' absence as a chance to 'spice up their marriage'.

Jake and Helen take the kids on a camping trip, which doesn't go well after Jake starts obsessing over his rocky relationship with his late father. Then it goes straight to hell when Jake, Helen and Quinn eat psychotropic berries and go insane. Meanwhile, Jane and Trent attend their dysfunctional family reunion.

Tommy Sherman, former Lawndale High football star, visits the school when a goalpost is named after him. He turns out to be a complete jerk that insults or propositions everyone he meets, particularly Daria, whom he calls a 'misery chick'. Daria and Jane crack a few jokes about wishing he were dead, and seconds later he ishuged when the goalpost falls on him. Suddenly everyone comes to Daria for advice on dealing with the traumatic incident, because they all think she's obsessed with passing, and Jane starts avoiding her because she feels responsible.